The best dog-friendly glamping near Bennington

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Ready to experience the great outdoors with your furry friends? Hipcamp has over 910 options for glamping with pets near Bennington, Vermont. Enjoy a luxurious camping experience while being surrounded by nature and your beloved pets. With options as low as $5 per night and an average price per night of $99, you'll find the perfect campsite for your budget. Check out top-rated campsites like Timbertrail Farm (257 reviews), Wyomanock Farm (215 reviews), and Quarry Brook (207 reviews). Popular amenities like showers, toilets, and trash are available, as well as activities such as fishing, swimming, and whitewater paddling. Book your glamping trip with Hipcamp today!

98% (4.3K)

Top-rated campgrounds

Salamander Hollow Healing Habitat

1. Salamander Hollow Healing Habitat

100%
(529)
46mi from Bennington · 5 sites · Lodging · Warwick, MA
Best HipCamp Massachusetts 2023 Best HipCamp USA Finalist 2023 Best HipCamp Massachusetts Finalist 2022 THERE IS WIFI, PRIVATE HOT SHOWER and FLUSH TOILET. EXCEPT FOR THE RECENTLY ADDED TULLY 'THOREAU' ISLAND. Salamander Hollow is a private, evolving honeybee and human being sanctuary on 17 acres of land abutting Massachusetts State Forest. We currently have a one-room, wood stove warmed, cozy sleeping loft for one or two - with two benches below on either side of room - for two sleeping bags; plus, a separate 22 foot Sioux tipi with two cots. There are two chairs in the tipi, which if removed at night, make floor room for four other sleeping bags. 'Forest Bathing' for miles! If you're a larger group booking Salamander Hollow main camp with its Sleeping Library, Tipi & Slovenian Beehive House, you might consider renting this additional Tiny Cabin want to entertain all in glamping style, utilizing its amenities; as well, providing another bathroom/shower and guest bedroom for those who prefer being indoors while in the great outdoors. Note that Kula Bata Tiny Cabin abuts the wheelchair accessible larger bathroom/shower which is available to those at the Salamander Hollow main camp, yet you are secluded with your own private entry points and private bathroom. A ten minute drive takes you to the parking area to hike up Tully Mountain. There is a grill, wood fired pizza oven, two fire pits and a hygienic Incinolet electric toilet on the property for night convenience, with small camp sinks for washing & teeth brushing. Take a short hike off the property to organic Chase Hill Farm for milk, eggs, seasonal veggies, grass fed meat and other goodies. Say hello to their cows, chickens, pigs, goats, pups and kids. Nestled across the road from Salamander Hollow is Timber Haven Farm, where you can schedule your pickup of bacon and eggs, while loading up on delicious Owl Energy Bars for your adventurous excursions. For those interested in the glamping side of camping, you will enjoy a remote rustic experience with a few creature comforts to keep you well read, clean and fed. Please bring your own bedding - pillows, sleeping bags, comforter, teddy bears.There is a wall mounted blue tooth car radio/CD player in Sleeping Library, so bring your pre-digital favorites. Classical CDs to listen to. Lots of eclectic books to peruse.Walkie talkies, a set of 4, are available upon request. Chess & poker sets, too. Electric 2-burner stovetop and griddle upon request. Bring fire-starters/newspaper for tinder. We suggest if you are staying more than a night or two in winter, you bring supplemental wood or we can direct you to a nearby stand. Next season, our own cut and split wood will be seasoned and available on site. We ask that you carry out trash and recyclables. An established Western facing four point sacred Medicine Wheel site being established on Askari Ridge - our name for the slope starting with the two fire pits - 'Askari' being Swahili for night guard. Here is where we envision a great touch-point area for those leading groups to be for a base-camp by day or night, where eventually a multi-use tenting platform/performance stage will be constructed for outdoor entertainment, creating an authentic 'stadium style' seating on the hill. You will see on your way up to Salamander Hollow main clearing - the Kula Bata Tiny Kabin on the left of the dirt road- now available to rent with its small guest room for two, infrared sauna, hot shower, kitchenette, dishwasher and laundry.
Potable water
Toilets
Campfires
from 
$75
 / night
Riverside Retreat and Tiny Cabin

3. Riverside Retreat and Tiny Cabin

100%
(43)
45mi from Bennington · 5 sites · Tents, RVs, Lodging · Poultney, VT
Refreshing riverside retreat with tent sites, RV/camper parking, and tiny house cabin on over 5 acres, featuring sunny meadows, veggie garden plot, 4-wheeler paths, and seasonal direct access to snowmobile trails. The property is perfectly nestled near the Green Mountains and the White Mountains, with a swimming hole and river fishing available right in the backyard. Bike trails, walking trails and stunning motorcycle routes are all at your fingertips from the property. Village amenities, such as groceries, bike shops, convenience stores, cafes, restaurants, and laundromat are all in walking distance (about 1 mile or less). Lake St. Catherine State Park (hot showers here) and Lake Bomoseen and others are close by for fun park activities. Visit a local winery (Whaleback Vineyard), see how maple syrup is made (Thrall Road Maple), shop the neighboring farm stands for local eggs, produce and baked goods. Close regional access to hunting, skiing, snowboarding. Leaf peeping season is here at the riverside retreat! The leaves are turning such lovely colors around here right now. Blackberries and fiddleheads on the property! In the fall, feel free to collect crab apples from our 100+ year old former orchard. *When in season. New additions: 6-seater triple hammock stand with built in picnic table. Fire pits and hammocks now at all sites! Tent sites can accommodate multiple tents, for group camping. Multiple fields available for yard games. Can accommodate parties and celebrations. 10’x10’ or 10’x20’ pop up shade tents available to rent upon request (with or without sidewalls). Excellent site for photo shoots, glamping, stargazing, sunbathing, leaf peeping, bachelor/ette parties. Want us to stock a cooler for you? Charcuterie, snacks, meals, beverages, etc. available upon request, customizable to your dietary preferences. Coming with a special guest? We can also provide flowers, sweet treats, custom greeting cards, etc.
Potable water
Toilets
Campfires
from 
$20
 / night
Upper Shire Campsites Hudson Valley

6. Upper Shire Campsites Hudson Valley

100%
(238)
47mi from Bennington · 7 sites · Tents, RVs, Lodging · Hillsdale, NY
The Upper Shire Private Campsites in the Hudson Valley are on a gorgeous hill with a small pond surrounded by 22 acres of an old horse ranch. It is located in Columbia County near the Massachusetts and New York border. There are currently 5 unique camping areas located here. Each one is special due to its location on the hill. Check out our map and enjoy our spacious yet secluded campsites and our new off-grid double shower shack with hot and cold water on demand. This place has a relaxed atmosphere and is located near Catamount Ski Resort, Bash Bish Falls, Taconic State Park, Hudson NY, and Great Barrington, MA. If you plan on bringing a pet please be sure to add that fee to your booking under "extras" ($25) If you have additional guest(s) that would like to join you that fee is ($25 a night per person) and you will need to message us about how to arrange that. We have extra easy pop-up two-person tents available to rent ($15 for two nights) you can also find that option under "extras" along with bundles of firewood ($15)
Potable water
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from 
$90
 / night
This is one of the views from Yon Barn.

8. Dickensen Farm: Cabins & Camping

98%
(144)
15mi from Bennington · 10 sites · Tents, RVs, Lodging · Cambridge, NY
Big Red Alpacas and Big Red Sustainables reside here at Dickensen Road in beautiful Cambridge NY close to both the Battenkill and Saratoga Springs. To help with the sustainability factor, we allow folks to camp on our property so they too can enjoy the woods, pastures, wild animals and farm animals, we all enjoy. Hence, we launched "Dickensen Farm: Cabins and Camping." The alpacas are inquisitive and peaceful animals, they are beautiful and provide wonderfully warm fashionable products as well. Please ask us about our seasonal products, including: Farm fresh, organically raised, free range chicken eggs Frozen meat birds Maple syrup Beautiful alpaca products Honey from our bees Dry, seasoned firewood for your camp sites Handmade Amish soaps However, you are not compelled to buy anything! If you are looking for a farmy or woodsy experience, we have BOTH at "Dickensen Farm: Cabins and Camping!"
Potable water
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from 
$36
 / night
Wyomanock Farm

9. Wyomanock Farm

97%
(844)
26mi from Bennington · 33 sites · Tents, RVs, Lodging · Stephentown, NY
Our 75 acres is a wonderful, diverse mix of habitat, harmoniously integrated with our small farm. This land was the homestead of the very first non native settler of the area, John Wiley, in 1787. Before that, it was the land of the Mahican native Americans. They named it "valley of the butternut trees", or Wyomanock. The Wyomanock Creek is the backbone of this little valley. Beaver have dammed the creek at several points to create ponds and other wetland features that support a diversity of wildlife including otter, moose and a myriad of birds, from osprey to herons. This sanctuary is host to many uncommon native plants and plant communities. We would love to share it with you! Your host, Thom, invites you to property to explore 75 acres of meadows, woods and water. Choose one of several sites either in the woods or open areas. You are also free to use our outdoor solar shower or take a dip in the cold pond or artesian spring fed pool. Our location is convenient to the Berkshire Mountains, state parks, hiking and other attractions, including Ramble Wild tree to tree adventures and Jiminy Peak. There are a few miles of rail trail access just down the road.
Potable water
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from 
$32
 / night
Dharma Bums Eco Lodge

10. Dharma Bums Eco Lodge

93%
(106)
32mi from Bennington · 11 sites · Tents, RVs, Lodging · Castleton On Hudson, NY
We have three different sites to choose from: Tiny House, Glamping, and Camp Site. Each is unique and private from each other! The bathroom is shared with the other sites, but it is covered and well maintained. Enjoy our private outdoor shower and toilet! Extras are available to purchase: firewood bundle, wine tasting and farm fresh eggs. All of our sites are animal friendly! Let your dog roam here! Our property sits on the foothills of the Adirondack's on 45 beautiful acres just 15 minutes east of Albany. Choose to explore our vineyard and winery on site and opt into our wine tasting next door. Open April-October, Friday-Sunday, 10-4pm Trails and walking paths are throughout the property and you may even catch our horses and honey bees that roam our beautiful community! Across the street is the Empire Foot/Rail Trails which is special for walking and biking. Local landmarks nearby and easy access to HWYs. Waterfalls and nice parks nearby Just a short distance away, our special community area that hosts yoga classes, and gathering sites: picnic tables, fire pits, gardens etc! We are just a short distance away from Troy and Albany
Potable water
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from 
$45
 / night
Cozy Mountain Cabin

11. Cozy Mountain Cabin

99%
(146)
15mi from Bennington · 1 site · Lodging · Arlington, VT
This off the grid cozy family owned cabin is located in the town of Sunderland, Vermont. Surrounded by hundreds of acres of national forest, campers can enjoy the sounds of a swift stream flowing nearby, birds chirping in trees, and the rustling of leaves and branches in the breeze. This mountainous area has a rich array of wildlife, meadows, trails, and only a few miles away from the Battenkill River, a tributary of the Hudson River of New York. Once inside you’ll find a small kitchen and dining area complete with a wood burning stove for those cool Vermont nights. The sleeping area offers four generously-sized bunks, a loft area, and a queen futon. Enjoy the peace of nature with a cup of coffee on the porch, but don’t forget to cap off the night with smores around the fire pit! Access to Vermont’s Long Trail System is nearby, with its 272 mile footpath and 166miles of side trails. This offers endless hiking opportunities for the day-hiker, weekend overnighter and extended backpacker. The Long Trail follows the main ridge of the Green Mountains from the Massachusetts-Vermont state line to the Canadian border, crossing Vermont’s highest peaks. As for the daily adventures, take a drive to surrounding ski resorts, including Bromley Mountain being just 15 miles from the property, where you can enjoy various activities year-round. Take a 10 minute drive to visit Mount Equinox Skyline drive where you’ll take in incredible views. Just past Mount Equinox is The Village of Manchester, which is home to the famed Equinox Resort and Spa. In Manchester, guests can enjoy everything from shopping & dining to outdoor classes for ATV driving and fly fishing!
Toilets
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Cooking equipment
from 
$94
 / night
Vermont Homestead

13. Vermont Homestead

100%
(4)
43mi from Bennington · 3 sites · Lodging · Chester, VT
This off-the-grid homestead sits on a quiet dirt road just outside the quaint village of Chester. Spread across 28 acres, the property features streams and trails to explore. The 8' x 14' Studio, complete with an accessible entry ramp, offers an elevated porch overlooking the garden, Adirondack chairs, an outdoor kitchen with table, grill and two-burner camp stove as well as a fire pit. Guests also have access to an accessible bathroom with a clawfoot tub located in the main house, about 250 feet from the Studio. An outdoor shower attached to the main house is also available. A wood-fired barrel sauna can be reserved for an additional charge. Frank, Julie, and their a very chill black Lab, Skye (who roams off-leash) welcome all visitors, from local to international, LGBTQ+, and those of all abilities. Chester itself offers a small grocery store, convenience store, a great coffee/sandwich shop, wine store, and several restaurants. Hiking trails are available both on the property and in the village, while Okemo Mountain, Mount Ascutney, and Lowell Lake State Park are just 20 minutes away. Manchester and Killington are approximately 45 minutes from the property.
Potable water
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from 
$80
 / night
Barge

14. Quentins Treehouse

97%
(158)
48mi from Bennington · 1 site · Lodging · Monterey, MA
About the Space Welcome to our lakeside treehouse retreat on the shores of historic Lake Garfield—named after President Garfield, who once summered here. This unique stay is tucked away in the beautiful Berkshires at 1,200 feet elevation, making for cool, crisp nights and star-filled skies. Originally the boatshed for the President’s summer home, the treehouse was built 15 years ago as a cozy sleepout perfect for stargazing and unwinding in nature. The Treehouse Perched in the trees and draped in wisteria, the treehouse features a clear corrugated roof, full flyscreening, and canvas blinds—keeping it breezy and bug-free. There’s a comfy hanging double bed with a high-quality mattress. Please note: guests need to bring their own sheets, bedding, and pillows. Amenities Portable camp toilet located beneath the treehouse Weber BBQ Wifi access Floating jetty & dock Two paddleboards for guests to enjoy Crystal-clear lake water (great for swimming, fishing, and boating) Things to Do We’re just a 15-minute drive from Great Barrington or Lee—ideal for dining, shopping, or exploring local culture. Incredible hiking trails are scattered throughout the surrounding area. Good to Know Please respect the natural surroundings—no damaging trees or leaving litter. Firewood bundles are available at nearby gas stations or directly from me. I look forward to welcoming you to this peaceful, magical space in the Berkshires.
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from 
$160
 / night
Spacious Skies Woodland Hills

16. Spacious Skies Woodland Hills

94%
(41)
39mi from Bennington · 158 sites · Tents, RVs, Lodging · Austerlitz, NY
SPACIOUS SKIES WOODLAND HILLS is a family-friendly campground located in upstate New York amidst the Taconic and Berkshire mountain ranges, set between Albany and Pittsfield, MA, and only two hours north of New York City and two hours west of Boston, MA. We offer both wooded and open sites that can accommodate any size trailer. Each site includes a picnic table, fire ring, water, 30 or 50-amp electrical service, and many offer sewer. Groups and tent campers are welcome. Woodland Hills campground is easily accessed from Interstate 90. The campground’s private pond offers swimming, fishing, and paddle boating. Come in for the classic camp atmosphere and our camp store carries many convenience items and treats. We have three Riverside Retro trailers to rent for campers who don’t have their own rigs but who also don’t want to tent overnight, as beautiful as our wooded tent sites are! * This campground does not have cabin rentals*
Potable water
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from 
$40
 / night
Going for a swim down at the nearby river! The trail right behind the barn takes you right there!

17. Fox Farm Campground

96%
(310)
30mi from Bennington · 8 sites · Tents, RVs, Lodging · Brattleboro, VT
Fox Farm is located on 8 magical acres in eclectic Brattleboro, VT. Pitch your tent in a sacred private white pine forest or closer to the trail-head with access to a charcoal grill, a huge fire circle and a picnic table. If you prefer a roof over your head, check Fox Farm Cottage @ Fox Farm. Located ideally on a trail-head that leads to the West River Trail (a 36-mile scenic trail through the West River Valley – eventually linking Brattleboro, Dummerston, Newfane, Townshend, Jamaica and South Londonderry) and the West River, offering opportunities to hike, fish, swim, ski, snow shoe and bike. The Marina Bar and Restaurant is a 2 mile hike or bike ride from the camp site (via the West River Trail) and is a fun way to see the beauty of Vermont and partake in some excellent indoor/outdoor dining with views of the water. Currently there are two areas available to campers; The Pine Forest and the Council of the Elders. The Pine Forest is a shaded circular area that is very spiritual and quiet. There are currently 3 camp sites in the Pine Forest. The Council of the Elders is a more open (again circular) area that abuts The Pine Forest and has a large fire pit as it's centerpiece, surrounded by the Elder Pine trees. I have had up to 2 campers and an occasional van/camper at the Council of the Elders. I have most recently had requests to book the entire Pine Forest for guests who are traveling together and want privacy- and Ido my best to work with people to accommodate any needs. Please bring your own firewood if you intend to have a fire. I offered wood to guests in the past when I was able but found that tricky to manage as there are times I myself am out of wood. There is plenty of felled wood all around as the property is surrounded by a dense forest and guests are welcome to gather that to supplement fire making. In my experience as a host, I have noted that folks come together and build mini-communities, share food, fires and is generally a positive vibe. Some come for privacy and solitude, which has not been an issue thus far. All in all the energy is upbeat and folks make friends along the way- me too! Brattleboro is a funky, hipster town with many excellent restaurants and much to see and do. For winter enthusiasts Mount Snow is a 30 minute drive and folks can cross country ski and snowshoe right from their camp sites to the 36 mile trail. The Hipcamper can expect privacy yet easy accessibility to the homeowner for tips and ideas to support a positive experience. Campers may be greeted and visited my friendly Bernese Mountain Dog's, Loki Bear and Levi!
Potable water
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from 
$65
 / night
Cherry Plain Sanctuary Farm

18. Cherry Plain Sanctuary Farm

100%
(14)
19mi from Bennington · 9 sites · Tents, Lodging · Cherry Plain, NY
Only 10 minutes from Cherry Plain State Park, Cherry Plain Sanctuary Farm/ Hearts in Hand Horsemanship LLC is a 150 acre hidden destination for outdoor adventurers, families and solo campers. We are a safe place for women who are traveling alone. We ensure everyone's quiet experience by not publishing our actual address. Please note: We ask for photo ID. Once we receive your photo ID via text we will provide exact directions to our property. Please plan to check in no later than 4:30pm as we are not available for later check ins unless we agree to meet you. It is dark at 5pm so early check in is critical. We host NYS Police along with local police/sheriff deputies here through our organization Hearts in Hand Horsemanship LLC. Don't be surprised if you see a NYS trooper or police unit parked up in the field near the horses. Fires: We allow small fires in specific spots, namely the fire ring at Camping on Blueberry Hill, at Ft Sky and inside the Tipi. Campsite fires are allowed weather permitting, when it's not windy and must be kept small. If it's windy then you can still have a fire in the tipi. No large fires or bonfires. All fires must be completely out unless you are physically with your fire. We supply 5 gallons of water and more is available to drink, wash dishes and put your fire out. Please respect our rules. Fire safety is necessary to keep everything safe here for all of us. Thank you for understanding. Here in the mountains we can experience very cold nights. We supply a small pile of firewood for a small fire at no charge. If you like, you can gather more dead wood (not live trees) in our forests. Winter is coming soon. Please bring lots of clothes and layers. Stay warm! Smoking: We are primarily a non-smoking/vaping farm and appreciate you smoking/vaping in your vehicle not on our premises please. Partying: Nope not us. Our farm is peaceful and quiet and so are our neighbors. Please party elsewhere and come here to relax in the blissful quiet of nature. Quiet music, just playing some Spotify tunes and acoustic musicians are welcome here. There's a great bar restaurant 5 minutes from us, "17 Cherry Plain Sq". Live music, great food and something like 40 beers on tap. Party there then chill out here with us. Breakfast and the best beef this side of the Mississippi can be found at Gardners Cafe and Icecream Shop only 5 miles up 22 South from our place. You can enjoy a big fat omelet with homefries and bacon then grab frozen hamburg and steaks from Gardner's own local beef grown wild and free outside. Cherry Plain Sanctuary Farm is adjacent to miles of public forest. Peace and solace can be found in these quiet mountains. In addition to amazing hiking, backpacking mountain biking, road biking right from your Hipcamp site, with kayaking nearby. We are 10 minutes away from Cherry Plain State Park (which has a gorgeous lake and kid-friendly sandy beach), and even closer to the Taconic Crest Trail. Our location is nestled between the Taconics of New York, the Green Mountains of Vermont, and the Berkshires of Massachusetts. Come share our paradise, bring your outdoor adventurer gear (you will be glad you did) and we will share our favorite local destinations with you. We ask that all hipcampers who are primary guests be 21 years of age or over. Children are welcome but we will not knowingly rent to anyone under 21 years of age. There is a $50 additional charge for garbage left at our farm including cigarette butts (we are a no smoking farm!), broken glass, bottles, cans, plastics, containers, bags and other trash. This is a pack in and pack out working farm not a party spot. Renting from us constitutes your reading of our rules attached to each property, your understanding and your agreement of our policies. Thank you so much for your understanding. We welcome you who seek quiet and the solace found in nature.
Potable water
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from 
$40
 / night
Shed has key pad access and pit toilet for use along with WI-FI and electricity. No running water but 5 gallons with manual pump provided. Water from natural spring up road near Dutch hill!

20. Touch Of Grey Stays

9.4mi from Bennington · 2 sites · Tents, Lodging · Stamford, VT
This listing is for a growing and ever-changing homestead property on a small hill overlooking our family home! We welcome those interested in learning more and engaging with us and the animals that live here to do so! We hope our guests will explore the property as we have trails looping throughout it, and look to build more over the years to come! We welcome well-mannered dogs off-leash on the property being mindful that it is located on a small hill overlooking our family home (Feather Pond Hollow on Instagram) which houses a toddler, two working-from-home adults, and as of July 2025, 2 White German Shepard/Great Pyrenees puppies (Bos and Ley who are 1 year old and learning), a chair lounging goat (Buttercup), 2 geese (the JuJus, good and bad - they can be, so best to be on guard), and many ducks and chickens. The wildflowers are in bloom for summer, and the song birds are singing. We invite you to join us in the woods! We are on Main Rd. (VT Route 8) and the property has a driveway entrance, making it easy to leave and explore the nearby areas of: South to Massachusetts: North Adams, MA (10 mins), which is home to Mass MoCA - the largest contemporary art museum in the country, and many wonderful spots to explore for shopping and dining. Williamstown, MA (20 mins), offers tons of hiking trails and The Clark museum. Staying in VT: Readsboro, VT (10 mins), has an out-of-this-world general store with food you don't expect to find in the woods; Readsboro General Store is a must-see, and sandwiches/salads you'll come back for! Readsboro Inn is the perfect place for an easy drive for drinks, a burger, or pizza, if you please! Wilmington, VT (20 mins), offers water activities, such as boating, swimming, and fishing! There are also hiking trails, like Mt. Olga in Molly State Park, and shopping on Main Street, flea market weekends, breweries, and fine dining can be found nearby. Snow Republic Brewery is a vibe worth basking in, in Dover, VT, north of Wilmington towards Mount Snow, where summer activities abound!
Potable water
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from 
$18
 / night

Ready to experience the great outdoors with your furry friends? Hipcamp has over 910 options for glamping with pets near Bennington, Vermont. Enjoy a luxurious camping experience while being surrounded by nature and your beloved pets. With options as low as $5 per night and an average price per night of $99, you'll find the perfect campsite for your budget. Check out top-rated campsites like Timbertrail Farm (257 reviews), Wyomanock Farm (215 reviews), and Quarry Brook (207 reviews). Popular amenities like showers, toilets, and trash are available, as well as activities such as fishing, swimming, and whitewater paddling. Book your glamping trip with Hipcamp today!

98% (4.3K)

Top-rated campgrounds

Salamander Hollow Healing Habitat

1. Salamander Hollow Healing Habitat

100%
(529)
46mi from Bennington · 5 sites · Lodging · Warwick, MA
Best HipCamp Massachusetts 2023 Best HipCamp USA Finalist 2023 Best HipCamp Massachusetts Finalist 2022 THERE IS WIFI, PRIVATE HOT SHOWER and FLUSH TOILET. EXCEPT FOR THE RECENTLY ADDED TULLY 'THOREAU' ISLAND. Salamander Hollow is a private, evolving honeybee and human being sanctuary on 17 acres of land abutting Massachusetts State Forest. We currently have a one-room, wood stove warmed, cozy sleeping loft for one or two - with two benches below on either side of room - for two sleeping bags; plus, a separate 22 foot Sioux tipi with two cots. There are two chairs in the tipi, which if removed at night, make floor room for four other sleeping bags. 'Forest Bathing' for miles! If you're a larger group booking Salamander Hollow main camp with its Sleeping Library, Tipi & Slovenian Beehive House, you might consider renting this additional Tiny Cabin want to entertain all in glamping style, utilizing its amenities; as well, providing another bathroom/shower and guest bedroom for those who prefer being indoors while in the great outdoors. Note that Kula Bata Tiny Cabin abuts the wheelchair accessible larger bathroom/shower which is available to those at the Salamander Hollow main camp, yet you are secluded with your own private entry points and private bathroom. A ten minute drive takes you to the parking area to hike up Tully Mountain. There is a grill, wood fired pizza oven, two fire pits and a hygienic Incinolet electric toilet on the property for night convenience, with small camp sinks for washing & teeth brushing. Take a short hike off the property to organic Chase Hill Farm for milk, eggs, seasonal veggies, grass fed meat and other goodies. Say hello to their cows, chickens, pigs, goats, pups and kids. Nestled across the road from Salamander Hollow is Timber Haven Farm, where you can schedule your pickup of bacon and eggs, while loading up on delicious Owl Energy Bars for your adventurous excursions. For those interested in the glamping side of camping, you will enjoy a remote rustic experience with a few creature comforts to keep you well read, clean and fed. Please bring your own bedding - pillows, sleeping bags, comforter, teddy bears.There is a wall mounted blue tooth car radio/CD player in Sleeping Library, so bring your pre-digital favorites. Classical CDs to listen to. Lots of eclectic books to peruse.Walkie talkies, a set of 4, are available upon request. Chess & poker sets, too. Electric 2-burner stovetop and griddle upon request. Bring fire-starters/newspaper for tinder. We suggest if you are staying more than a night or two in winter, you bring supplemental wood or we can direct you to a nearby stand. Next season, our own cut and split wood will be seasoned and available on site. We ask that you carry out trash and recyclables. An established Western facing four point sacred Medicine Wheel site being established on Askari Ridge - our name for the slope starting with the two fire pits - 'Askari' being Swahili for night guard. Here is where we envision a great touch-point area for those leading groups to be for a base-camp by day or night, where eventually a multi-use tenting platform/performance stage will be constructed for outdoor entertainment, creating an authentic 'stadium style' seating on the hill. You will see on your way up to Salamander Hollow main clearing - the Kula Bata Tiny Kabin on the left of the dirt road- now available to rent with its small guest room for two, infrared sauna, hot shower, kitchenette, dishwasher and laundry.
Potable water
Toilets
Campfires
from 
$75
 / night
Riverside Retreat and Tiny Cabin

3. Riverside Retreat and Tiny Cabin

100%
(43)
45mi from Bennington · 5 sites · Tents, RVs, Lodging · Poultney, VT
Refreshing riverside retreat with tent sites, RV/camper parking, and tiny house cabin on over 5 acres, featuring sunny meadows, veggie garden plot, 4-wheeler paths, and seasonal direct access to snowmobile trails. The property is perfectly nestled near the Green Mountains and the White Mountains, with a swimming hole and river fishing available right in the backyard. Bike trails, walking trails and stunning motorcycle routes are all at your fingertips from the property. Village amenities, such as groceries, bike shops, convenience stores, cafes, restaurants, and laundromat are all in walking distance (about 1 mile or less). Lake St. Catherine State Park (hot showers here) and Lake Bomoseen and others are close by for fun park activities. Visit a local winery (Whaleback Vineyard), see how maple syrup is made (Thrall Road Maple), shop the neighboring farm stands for local eggs, produce and baked goods. Close regional access to hunting, skiing, snowboarding. Leaf peeping season is here at the riverside retreat! The leaves are turning such lovely colors around here right now. Blackberries and fiddleheads on the property! In the fall, feel free to collect crab apples from our 100+ year old former orchard. *When in season. New additions: 6-seater triple hammock stand with built in picnic table. Fire pits and hammocks now at all sites! Tent sites can accommodate multiple tents, for group camping. Multiple fields available for yard games. Can accommodate parties and celebrations. 10’x10’ or 10’x20’ pop up shade tents available to rent upon request (with or without sidewalls). Excellent site for photo shoots, glamping, stargazing, sunbathing, leaf peeping, bachelor/ette parties. Want us to stock a cooler for you? Charcuterie, snacks, meals, beverages, etc. available upon request, customizable to your dietary preferences. Coming with a special guest? We can also provide flowers, sweet treats, custom greeting cards, etc.
Potable water
Toilets
Campfires
from 
$20
 / night
Upper Shire Campsites Hudson Valley

6. Upper Shire Campsites Hudson Valley

100%
(238)
47mi from Bennington · 7 sites · Tents, RVs, Lodging · Hillsdale, NY
The Upper Shire Private Campsites in the Hudson Valley are on a gorgeous hill with a small pond surrounded by 22 acres of an old horse ranch. It is located in Columbia County near the Massachusetts and New York border. There are currently 5 unique camping areas located here. Each one is special due to its location on the hill. Check out our map and enjoy our spacious yet secluded campsites and our new off-grid double shower shack with hot and cold water on demand. This place has a relaxed atmosphere and is located near Catamount Ski Resort, Bash Bish Falls, Taconic State Park, Hudson NY, and Great Barrington, MA. If you plan on bringing a pet please be sure to add that fee to your booking under "extras" ($25) If you have additional guest(s) that would like to join you that fee is ($25 a night per person) and you will need to message us about how to arrange that. We have extra easy pop-up two-person tents available to rent ($15 for two nights) you can also find that option under "extras" along with bundles of firewood ($15)
Potable water
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Campfires
from 
$90
 / night
This is one of the views from Yon Barn.

8. Dickensen Farm: Cabins & Camping

98%
(144)
15mi from Bennington · 10 sites · Tents, RVs, Lodging · Cambridge, NY
Big Red Alpacas and Big Red Sustainables reside here at Dickensen Road in beautiful Cambridge NY close to both the Battenkill and Saratoga Springs. To help with the sustainability factor, we allow folks to camp on our property so they too can enjoy the woods, pastures, wild animals and farm animals, we all enjoy. Hence, we launched "Dickensen Farm: Cabins and Camping." The alpacas are inquisitive and peaceful animals, they are beautiful and provide wonderfully warm fashionable products as well. Please ask us about our seasonal products, including: Farm fresh, organically raised, free range chicken eggs Frozen meat birds Maple syrup Beautiful alpaca products Honey from our bees Dry, seasoned firewood for your camp sites Handmade Amish soaps However, you are not compelled to buy anything! If you are looking for a farmy or woodsy experience, we have BOTH at "Dickensen Farm: Cabins and Camping!"
Potable water
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from 
$36
 / night
Wyomanock Farm

9. Wyomanock Farm

97%
(844)
26mi from Bennington · 33 sites · Tents, RVs, Lodging · Stephentown, NY
Our 75 acres is a wonderful, diverse mix of habitat, harmoniously integrated with our small farm. This land was the homestead of the very first non native settler of the area, John Wiley, in 1787. Before that, it was the land of the Mahican native Americans. They named it "valley of the butternut trees", or Wyomanock. The Wyomanock Creek is the backbone of this little valley. Beaver have dammed the creek at several points to create ponds and other wetland features that support a diversity of wildlife including otter, moose and a myriad of birds, from osprey to herons. This sanctuary is host to many uncommon native plants and plant communities. We would love to share it with you! Your host, Thom, invites you to property to explore 75 acres of meadows, woods and water. Choose one of several sites either in the woods or open areas. You are also free to use our outdoor solar shower or take a dip in the cold pond or artesian spring fed pool. Our location is convenient to the Berkshire Mountains, state parks, hiking and other attractions, including Ramble Wild tree to tree adventures and Jiminy Peak. There are a few miles of rail trail access just down the road.
Potable water
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from 
$32
 / night
Dharma Bums Eco Lodge

10. Dharma Bums Eco Lodge

93%
(106)
32mi from Bennington · 11 sites · Tents, RVs, Lodging · Castleton On Hudson, NY
We have three different sites to choose from: Tiny House, Glamping, and Camp Site. Each is unique and private from each other! The bathroom is shared with the other sites, but it is covered and well maintained. Enjoy our private outdoor shower and toilet! Extras are available to purchase: firewood bundle, wine tasting and farm fresh eggs. All of our sites are animal friendly! Let your dog roam here! Our property sits on the foothills of the Adirondack's on 45 beautiful acres just 15 minutes east of Albany. Choose to explore our vineyard and winery on site and opt into our wine tasting next door. Open April-October, Friday-Sunday, 10-4pm Trails and walking paths are throughout the property and you may even catch our horses and honey bees that roam our beautiful community! Across the street is the Empire Foot/Rail Trails which is special for walking and biking. Local landmarks nearby and easy access to HWYs. Waterfalls and nice parks nearby Just a short distance away, our special community area that hosts yoga classes, and gathering sites: picnic tables, fire pits, gardens etc! We are just a short distance away from Troy and Albany
Potable water
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from 
$45
 / night
Cozy Mountain Cabin

11. Cozy Mountain Cabin

99%
(146)
15mi from Bennington · 1 site · Lodging · Arlington, VT
This off the grid cozy family owned cabin is located in the town of Sunderland, Vermont. Surrounded by hundreds of acres of national forest, campers can enjoy the sounds of a swift stream flowing nearby, birds chirping in trees, and the rustling of leaves and branches in the breeze. This mountainous area has a rich array of wildlife, meadows, trails, and only a few miles away from the Battenkill River, a tributary of the Hudson River of New York. Once inside you’ll find a small kitchen and dining area complete with a wood burning stove for those cool Vermont nights. The sleeping area offers four generously-sized bunks, a loft area, and a queen futon. Enjoy the peace of nature with a cup of coffee on the porch, but don’t forget to cap off the night with smores around the fire pit! Access to Vermont’s Long Trail System is nearby, with its 272 mile footpath and 166miles of side trails. This offers endless hiking opportunities for the day-hiker, weekend overnighter and extended backpacker. The Long Trail follows the main ridge of the Green Mountains from the Massachusetts-Vermont state line to the Canadian border, crossing Vermont’s highest peaks. As for the daily adventures, take a drive to surrounding ski resorts, including Bromley Mountain being just 15 miles from the property, where you can enjoy various activities year-round. Take a 10 minute drive to visit Mount Equinox Skyline drive where you’ll take in incredible views. Just past Mount Equinox is The Village of Manchester, which is home to the famed Equinox Resort and Spa. In Manchester, guests can enjoy everything from shopping & dining to outdoor classes for ATV driving and fly fishing!
Toilets
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Cooking equipment
from 
$94
 / night
Vermont Homestead

13. Vermont Homestead

100%
(4)
43mi from Bennington · 3 sites · Lodging · Chester, VT
This off-the-grid homestead sits on a quiet dirt road just outside the quaint village of Chester. Spread across 28 acres, the property features streams and trails to explore. The 8' x 14' Studio, complete with an accessible entry ramp, offers an elevated porch overlooking the garden, Adirondack chairs, an outdoor kitchen with table, grill and two-burner camp stove as well as a fire pit. Guests also have access to an accessible bathroom with a clawfoot tub located in the main house, about 250 feet from the Studio. An outdoor shower attached to the main house is also available. A wood-fired barrel sauna can be reserved for an additional charge. Frank, Julie, and their a very chill black Lab, Skye (who roams off-leash) welcome all visitors, from local to international, LGBTQ+, and those of all abilities. Chester itself offers a small grocery store, convenience store, a great coffee/sandwich shop, wine store, and several restaurants. Hiking trails are available both on the property and in the village, while Okemo Mountain, Mount Ascutney, and Lowell Lake State Park are just 20 minutes away. Manchester and Killington are approximately 45 minutes from the property.
Potable water
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from 
$80
 / night
Barge

14. Quentins Treehouse

97%
(158)
48mi from Bennington · 1 site · Lodging · Monterey, MA
About the Space Welcome to our lakeside treehouse retreat on the shores of historic Lake Garfield—named after President Garfield, who once summered here. This unique stay is tucked away in the beautiful Berkshires at 1,200 feet elevation, making for cool, crisp nights and star-filled skies. Originally the boatshed for the President’s summer home, the treehouse was built 15 years ago as a cozy sleepout perfect for stargazing and unwinding in nature. The Treehouse Perched in the trees and draped in wisteria, the treehouse features a clear corrugated roof, full flyscreening, and canvas blinds—keeping it breezy and bug-free. There’s a comfy hanging double bed with a high-quality mattress. Please note: guests need to bring their own sheets, bedding, and pillows. Amenities Portable camp toilet located beneath the treehouse Weber BBQ Wifi access Floating jetty & dock Two paddleboards for guests to enjoy Crystal-clear lake water (great for swimming, fishing, and boating) Things to Do We’re just a 15-minute drive from Great Barrington or Lee—ideal for dining, shopping, or exploring local culture. Incredible hiking trails are scattered throughout the surrounding area. Good to Know Please respect the natural surroundings—no damaging trees or leaving litter. Firewood bundles are available at nearby gas stations or directly from me. I look forward to welcoming you to this peaceful, magical space in the Berkshires.
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$160
 / night
Spacious Skies Woodland Hills

16. Spacious Skies Woodland Hills

94%
(41)
39mi from Bennington · 158 sites · Tents, RVs, Lodging · Austerlitz, NY
SPACIOUS SKIES WOODLAND HILLS is a family-friendly campground located in upstate New York amidst the Taconic and Berkshire mountain ranges, set between Albany and Pittsfield, MA, and only two hours north of New York City and two hours west of Boston, MA. We offer both wooded and open sites that can accommodate any size trailer. Each site includes a picnic table, fire ring, water, 30 or 50-amp electrical service, and many offer sewer. Groups and tent campers are welcome. Woodland Hills campground is easily accessed from Interstate 90. The campground’s private pond offers swimming, fishing, and paddle boating. Come in for the classic camp atmosphere and our camp store carries many convenience items and treats. We have three Riverside Retro trailers to rent for campers who don’t have their own rigs but who also don’t want to tent overnight, as beautiful as our wooded tent sites are! * This campground does not have cabin rentals*
Potable water
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from 
$40
 / night
Going for a swim down at the nearby river! The trail right behind the barn takes you right there!

17. Fox Farm Campground

96%
(310)
30mi from Bennington · 8 sites · Tents, RVs, Lodging · Brattleboro, VT
Fox Farm is located on 8 magical acres in eclectic Brattleboro, VT. Pitch your tent in a sacred private white pine forest or closer to the trail-head with access to a charcoal grill, a huge fire circle and a picnic table. If you prefer a roof over your head, check Fox Farm Cottage @ Fox Farm. Located ideally on a trail-head that leads to the West River Trail (a 36-mile scenic trail through the West River Valley – eventually linking Brattleboro, Dummerston, Newfane, Townshend, Jamaica and South Londonderry) and the West River, offering opportunities to hike, fish, swim, ski, snow shoe and bike. The Marina Bar and Restaurant is a 2 mile hike or bike ride from the camp site (via the West River Trail) and is a fun way to see the beauty of Vermont and partake in some excellent indoor/outdoor dining with views of the water. Currently there are two areas available to campers; The Pine Forest and the Council of the Elders. The Pine Forest is a shaded circular area that is very spiritual and quiet. There are currently 3 camp sites in the Pine Forest. The Council of the Elders is a more open (again circular) area that abuts The Pine Forest and has a large fire pit as it's centerpiece, surrounded by the Elder Pine trees. I have had up to 2 campers and an occasional van/camper at the Council of the Elders. I have most recently had requests to book the entire Pine Forest for guests who are traveling together and want privacy- and Ido my best to work with people to accommodate any needs. Please bring your own firewood if you intend to have a fire. I offered wood to guests in the past when I was able but found that tricky to manage as there are times I myself am out of wood. There is plenty of felled wood all around as the property is surrounded by a dense forest and guests are welcome to gather that to supplement fire making. In my experience as a host, I have noted that folks come together and build mini-communities, share food, fires and is generally a positive vibe. Some come for privacy and solitude, which has not been an issue thus far. All in all the energy is upbeat and folks make friends along the way- me too! Brattleboro is a funky, hipster town with many excellent restaurants and much to see and do. For winter enthusiasts Mount Snow is a 30 minute drive and folks can cross country ski and snowshoe right from their camp sites to the 36 mile trail. The Hipcamper can expect privacy yet easy accessibility to the homeowner for tips and ideas to support a positive experience. Campers may be greeted and visited my friendly Bernese Mountain Dog's, Loki Bear and Levi!
Potable water
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from 
$65
 / night
Cherry Plain Sanctuary Farm

18. Cherry Plain Sanctuary Farm

100%
(14)
19mi from Bennington · 9 sites · Tents, Lodging · Cherry Plain, NY
Only 10 minutes from Cherry Plain State Park, Cherry Plain Sanctuary Farm/ Hearts in Hand Horsemanship LLC is a 150 acre hidden destination for outdoor adventurers, families and solo campers. We are a safe place for women who are traveling alone. We ensure everyone's quiet experience by not publishing our actual address. Please note: We ask for photo ID. Once we receive your photo ID via text we will provide exact directions to our property. Please plan to check in no later than 4:30pm as we are not available for later check ins unless we agree to meet you. It is dark at 5pm so early check in is critical. We host NYS Police along with local police/sheriff deputies here through our organization Hearts in Hand Horsemanship LLC. Don't be surprised if you see a NYS trooper or police unit parked up in the field near the horses. Fires: We allow small fires in specific spots, namely the fire ring at Camping on Blueberry Hill, at Ft Sky and inside the Tipi. Campsite fires are allowed weather permitting, when it's not windy and must be kept small. If it's windy then you can still have a fire in the tipi. No large fires or bonfires. All fires must be completely out unless you are physically with your fire. We supply 5 gallons of water and more is available to drink, wash dishes and put your fire out. Please respect our rules. Fire safety is necessary to keep everything safe here for all of us. Thank you for understanding. Here in the mountains we can experience very cold nights. We supply a small pile of firewood for a small fire at no charge. If you like, you can gather more dead wood (not live trees) in our forests. Winter is coming soon. Please bring lots of clothes and layers. Stay warm! Smoking: We are primarily a non-smoking/vaping farm and appreciate you smoking/vaping in your vehicle not on our premises please. Partying: Nope not us. Our farm is peaceful and quiet and so are our neighbors. Please party elsewhere and come here to relax in the blissful quiet of nature. Quiet music, just playing some Spotify tunes and acoustic musicians are welcome here. There's a great bar restaurant 5 minutes from us, "17 Cherry Plain Sq". Live music, great food and something like 40 beers on tap. Party there then chill out here with us. Breakfast and the best beef this side of the Mississippi can be found at Gardners Cafe and Icecream Shop only 5 miles up 22 South from our place. You can enjoy a big fat omelet with homefries and bacon then grab frozen hamburg and steaks from Gardner's own local beef grown wild and free outside. Cherry Plain Sanctuary Farm is adjacent to miles of public forest. Peace and solace can be found in these quiet mountains. In addition to amazing hiking, backpacking mountain biking, road biking right from your Hipcamp site, with kayaking nearby. We are 10 minutes away from Cherry Plain State Park (which has a gorgeous lake and kid-friendly sandy beach), and even closer to the Taconic Crest Trail. Our location is nestled between the Taconics of New York, the Green Mountains of Vermont, and the Berkshires of Massachusetts. Come share our paradise, bring your outdoor adventurer gear (you will be glad you did) and we will share our favorite local destinations with you. We ask that all hipcampers who are primary guests be 21 years of age or over. Children are welcome but we will not knowingly rent to anyone under 21 years of age. There is a $50 additional charge for garbage left at our farm including cigarette butts (we are a no smoking farm!), broken glass, bottles, cans, plastics, containers, bags and other trash. This is a pack in and pack out working farm not a party spot. Renting from us constitutes your reading of our rules attached to each property, your understanding and your agreement of our policies. Thank you so much for your understanding. We welcome you who seek quiet and the solace found in nature.
Potable water
Toilets
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from 
$40
 / night
Shed has key pad access and pit toilet for use along with WI-FI and electricity. No running water but 5 gallons with manual pump provided. Water from natural spring up road near Dutch hill!

20. Touch Of Grey Stays

9.4mi from Bennington · 2 sites · Tents, Lodging · Stamford, VT
This listing is for a growing and ever-changing homestead property on a small hill overlooking our family home! We welcome those interested in learning more and engaging with us and the animals that live here to do so! We hope our guests will explore the property as we have trails looping throughout it, and look to build more over the years to come! We welcome well-mannered dogs off-leash on the property being mindful that it is located on a small hill overlooking our family home (Feather Pond Hollow on Instagram) which houses a toddler, two working-from-home adults, and as of July 2025, 2 White German Shepard/Great Pyrenees puppies (Bos and Ley who are 1 year old and learning), a chair lounging goat (Buttercup), 2 geese (the JuJus, good and bad - they can be, so best to be on guard), and many ducks and chickens. The wildflowers are in bloom for summer, and the song birds are singing. We invite you to join us in the woods! We are on Main Rd. (VT Route 8) and the property has a driveway entrance, making it easy to leave and explore the nearby areas of: South to Massachusetts: North Adams, MA (10 mins), which is home to Mass MoCA - the largest contemporary art museum in the country, and many wonderful spots to explore for shopping and dining. Williamstown, MA (20 mins), offers tons of hiking trails and The Clark museum. Staying in VT: Readsboro, VT (10 mins), has an out-of-this-world general store with food you don't expect to find in the woods; Readsboro General Store is a must-see, and sandwiches/salads you'll come back for! Readsboro Inn is the perfect place for an easy drive for drinks, a burger, or pizza, if you please! Wilmington, VT (20 mins), offers water activities, such as boating, swimming, and fishing! There are also hiking trails, like Mt. Olga in Molly State Park, and shopping on Main Street, flea market weekends, breweries, and fine dining can be found nearby. Snow Republic Brewery is a vibe worth basking in, in Dover, VT, north of Wilmington towards Mount Snow, where summer activities abound!
Potable water
Toilets
Campfires
from 
$18
 / night

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