Glamping near Winchester Center

·
95% (1.9K)

Top-rated campgrounds

Humble Farm with Simplicity

1. Humble Farm with Simplicity

96%
(212)
44mi from Winchester Center · 10 sites · Tents, RVs, Lodging · Higganum, CT
Bring your family and friends to camp at our quiet and very earthy and modest small family farm. Located in backwoods horse pastures with chickens, a dog, and a few horses. The property is very spread out and there are 2 outhouses for all sites to use. Your pets are welcome too! Locally there are state parks with beaches, and state forest for trails and lakes, hiking and biking. Or you can just relax and enjoy the serenity! OUR ADDRESS IS #200 NOT #204 Two parallel driveways THE DRIVEWAY TO THE LEFT FROM THE STREET IS OURS. Other attractions include local farmers markets, Millers Pond, Hammonassette State Park Beach, Gilette's Castle, with the famous River Ferry crossing the Connecticut River with a vehicle across to East Haddam at end of Rt. 148... We offer an hot H2O outdoor shower here for the comfort of out clients. It is located on the back of main house in corner. Entrance through gate is marked. Also See map in photos. We cannot allow any wood for camp fires to be brought in form the outside for environmental reasons. It can be pre-purchased for $12 per bundle on this site, or $10.00 cash here at farm. Farm Fresh eggs daily when available for $5.00 per 1/2 dozen. Blankets and pillows only are provided, NO LINENS for cabin or trailer sites only. Garbage removal is available as well $5 per bag provided.
Pets
Potable water
Toilets
from 
$49
 / night
two story tiny cabin with two windows on bottom floor and two screened windows on top floor that can open

2. Atland Artist Residency

100%
(110)
37mi from Winchester Center · 9 sites · Tents, Lodging · West Chesterfield, MA
We're named one of the best Hipcamps to visit in 2024 and 2023! Over 40 acres of solitude tucked in the hilltowns of the western Massachusetts Berkshires -- boasting warm sunrises over the distant hills, lush forest for hiking and meandering river frontage on Bronson Brook and walking distance to the Westfield River to wade and soak in the cool mountain water or fish for native trout! The cabin and camping sites are located in beautiful trails that were created around the main home -- an architect designed masterpiece boasting a wonderful asian influence yet handcrafted from the very timberstock off the land on which it sits lending a refined rustic twist. 25 Min to Northampton and 10 min to the Berkshires! You can hike or bike to the best swimming holes around and camp within our beautiful forested hills of hemlock, birch, maple, and wildflower meadow. If you're into kayaking/canoeing/tubing/hiking/fishing, then this is the perfect space for you. Come escape and breathe in our cool clean mountain air :)
Pets
Potable water
Toilets
from 
$45
 / night
Woodland's Edge Glamping & Hot Tubs

3. Woodland's Edge Glamping & Hot Tubs

90%
(109)
46mi from Winchester Center · 3 sites · Lodging · Belchertown, MA
Choose between our extra large tent can hold a family/friend group of up to 8 comfortably, but is also cozy enough for a couple's getaway. Or our sweet-as-can-be tiny A-frame cabin. Our private site is in the middle of a mixed-wood forest. Deer roam free and you will surely hear the call of coyotes and owls at night. Centrally located within 10 minutes of downtown Amherst, 15 minutes to downtown Northampton, this tent is the perfect base camp to access all that this region has to offer. Flea markets and farmers markets on the weekends, malls, museums and numerous restaurants in the area should you decide to venture out for a bite to eat. Holland Glen, a popular hiking spot with waterfalls and swimming holes is a quick 3-minute drive to the trail head. It is an easy 1-mile ride to the start of the Norwotuck Rail Trail a paved bike path through wetlands and rolling farmland. Or simply stay put, unplug, and relax in one of the hammocks or enjoy our one of a kind wood-fired hot tubs! Our guests are welcome to wander around our little homestead have your coffee in the pollinator patch and watch the hummingbirds, butterflies and bees do their thing. Feed the chickens, then nibble your way through our berry patches, fruit trees and gardens and experience what it is like to live simply in New England. Cook a meal over the fire - we will provide the cast iron pans and dishes if needed. Learn more about this land: A private campsite on the edge of a woodland forest. Deer roam free and you will surely hear the coyotes call at night. Centrally located within minutes of Amherst and Northampton, this tent is the perfect base camp to this vibrant region. Relax in the hammock with a good book, play a rowdy game of corn hole, sip your coffee in our pollinator patch, tell stories by the campfire or rent our projector for the night for a fun in-tent movie!
Potable water
Toilets
Campfires
from 
$77
 / night
Upper Shire Campsites Hudson Valley

7. Upper Shire Campsites Hudson Valley

100%
(238)
29mi from Winchester Center · 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)
Pets
Potable water
Toilets
from 
$90
 / night
Wyomanock Farm

8. Wyomanock Farm

97%
(844)
44mi from Winchester Center · 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.
Pets
Potable water
Toilets
from 
$32
 / night
The Awakening Garden

9. The Awakening Garden

100%
(10)
48mi from Winchester Center · 4 sites · Lodging · Saugerties, NY
This piece of land was developed by my mother, and named after my grandmother: The Awakening Garden is a translation of her name in Chinese. It is tucked in between the Hudson River (8 miles to the East) and the Catskill Mountains (10 miles to the west). It is just 6 miles from the Village of Saugerties and 14 miles to Woodstock, NY. The piece available for camping is 10 acres, but the entire Garden is comprised of 98 acres of rolling land (most of it in a forestry protection plan) bordered on the west by acres of marshland. Many trails criss-cross the Garden and lead one to pretty or interesting vistas including a large mountain laurel patch, ancient graveyard, and different stands of mixed wood forests. There’s lots of wildlife both on land and in the marshes.
Pets
Potable water
Toilets
from 
$93
 / night
Magical Yurt in the Woods

14. Magical Yurt in the Woods

100%
(5)
42mi from Winchester Center · 1 site · Lodging · Williamsburg, MA
A magical place in the woods inviting a return to your essential nature located amongst watershed land in Williamsburg, MA. Simple, quiet, and cozy. The space works in many wonderful ways, especially as a vessel for nurturing self-directed retreats like writing or meditation retreats. Many local trails including The Holyoke Range, The Berkshires Mountains, Graves Brothers Loop Trail, and Petticoat Hill Trail Loop. Experience nature, trails, starry nights, and hooting owls. The Yurt is located a twenty-minute drive from the vibrant downtown of Northampton, MA. The Yurt is a wonderful place for parents to stay when your kid graduates from one of the Five Colleges: Smith College, Amherst, Mt.Holyoke, Hampshire, and U. MASS. The Yurt is a short drive from MASS MoCA, Green River music festival, Tanglewood music festival, and Jacob’s Pillow. What have previous Yurtlings said about this space? "We came to celebrate a birthday and, within that, generate a shared transcendent experience. The yurt is the ideal container to hold such a ceremonial and sacred journey. The weekend was more than we could have hoped for! Thank you Carolyn! In Unity + Gratitude, Sara + Pete" "At night we heard barred owls calling out, it reminded that quiet isn't silent, and the darkness has layers, it is never just one thing. ❤️Cate and Em" We are extremely blessed to live in the woods amongst watershed land and hooting owls. With nothing but star-lit skies, I’m delighted to extend this sliver of natural beauty to you.
Potable water
Toilets
Showers
from 
$125
 / night
The trails through the forest offer a nice place to stroll.

15. Sunflower Retreat

99%
(103)
39mi from Winchester Center · 1 site · Lodging · Cummington, MA
A humble, 2-acre vegetarian family micro farm. Home to our family of five, 2 cats, 2 rabbits and nineteen chickens. Beautiful, established flower gardens, fruit trees and veggies. This is also home to Sunflower Yoga & Mindfulness where yoga and meditation are taught. The cabin is nestled in the 1 acre of woods behind our home, protected by large old pines and surrounding acres of forest. Home to many songbirds, woodpeckers, raven, deer, porcupine and the occasional black bear. A true retreat. Small, rustic cabin with electricity in the woods behind our home in the hilltowns of Western Massachusetts. You are just 300 feet from the house, but while in the woods you will have complete privacy. The woods are filled with songbirds and there is a small platform for meditation. There is no wifi in the cabin, so enjoy the ability to disconnect from it all while connecting within. The hilltown region is rich with rivers and lakes for swimming, boating and fishing and forests for hiking. We are just 30 min to Northampton and 45min-1hour from the many cultural offerings of the Berkshires.
Potable water
Toilets
from 
$68
 / night
The full bathroom is on the back end of Howards house.

16. Sacred Hollow in Heart of Hudson

91%
(22)
49mi from Winchester Center · 4 sites · Tents, RVs, Lodging · Hurley, NY
the locals know our street because of the indigenous people and early Dutch settlers mixing with the slaves. Much history here, with the small town of stone houses, making Hurley a national historic destination. This serene is secluded on a mountain surrounded by trees with seasonal views. The campsite is neighboring 105 acres of beautiful conservatory land available for hiking. No true trails are available, but you can be adventurous and hike further up the mountain, arriving to a clearing, providing you with a lovely mountainous view. From the mountain, you can hike to a waterfall or even hike across a lovely plain field surrounded by mountain ranges on both sides and crossing the creek over to Historic Stone houses in Hurley. Within a 10 minute drive check out some of the local restaurants like Alebrijes, Hickory BBQ & Smokehouse, and the Hurley Inn where the movie “Tootsie” was filmed!. Hurley Marbletown Trailhead and Rail trail parking are only a 6 minute drive away! The town of Kingston is about 15 minutes from our site where you will find Bluestone Wild Forest, antique shops, restaurants, other outdoor activities! The nights are just spectacular as you look into the sky surrounded by a blanket of stars, able to see the many constellations looking like jewels on a black cloth. The sounds of nature and all of it's distinct calls including that of eagles, is truly an experience. And we cannot forget our other friendly neighbors, the wild turkeys and deer! We are very appreciative of this beauty and would love to share this sacred place with you. Learn more about this land: Feels like you’re away from civilization but yet close to all the Hudson valley has to offer. 15-20min from Woodstock, rosendale, stone ridge, Rhinebeck, red hook, New Paltz and Mohawnk short 30 min drive. The glampsite is a yurt with a fire pit and a full modern bathroom just a short walk away. For a small fee, you can also rent our bikes for riding the nearby rail trail or just visit the waterfall 2 miles away. Wood available for purchase. THE HOT TUB IS PART OF A MINI-SPA PACKAGE AAND IS AVAILABLE FOR AN ADDITIONAL FEE. Not only will You be relaxing, but also connecting with the cosmos through a 1 hr transformative healing session offered by the host for an extra fee.
Pets
Potable water
Toilets
from 
$54
 / night
Quentins Treehouse

17. Quentins Treehouse

97%
(158)
19mi from Winchester Center · 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.
Pets
Toilets
Campfires
from 
$160
 / night
The Catskill And Chill

18. The Catskill And Chill

95%
(38)
46mi from Winchester Center · 1 site · Lodging · Catskill, NY
Located In upstate New York is this hidden gem. This camper was old school, now turned new. With a full renovation to give it a Scandinavian look in the front, and a cozy cabin feel in the bedroom. This will give you a unique experience different from the normal camper your used to! Also at your campsite there is a firepit, garden hose,(not available during the winter)and a 8x8 hammock perfect to stargaze in! We are now offering kindling firewood with fire starter and matches. Feel free to reserve your own firewood. $10 *PLEASE READ THIS BEFORE BOOKING* I want to be transparent with you guys on the property and size of the camper! -The camper is very small only 21ft. The average height clearance is 6'2" so if you are tall this may not be for you. (I'm 5'9" and its comfortable for me) -If you are a bigger person this may feel too tight for you especially in the bathroom area -The bed is a full size some couples may feel that this is to small for them. -A hot shower will last about 15 minutes once it is heated up. -In the summertime there is bugs some may get into the camper. We do treat the area with safe bug spray but it may not fully prevent them. -There are two other tiny houses and a main house on the property. They are far apart but the main house is close. We have a privacy fence that fully blocks the house. So you are still very private but you are not fully secluded. -In case of fire There is a fire blanket, fire extinguisher, and a smoke/carbon monoxide detector inside the camper. The bedroom door is only to be used as an emergency fire exit. (Door is locked from the outside but unlocked from the inside) There is also a water cannon outside for outdoor fires. Please be responsible with all fires! -If you want to cancel you must cancel within 24 hours of booking then I will issue a full refund. Any time after that its a strict policy and no refund will be issued. Thank you for reading this I want to make sure everyone is aware and knows what to expect. Its still an awesome place and people love it! Hope this helps! OTHER AMMENDITIES INCLUDED: Bottled water Wifi Heating Air conditioning Fan and air purifier First Aid kit Fire extinguisher, fire blanket, water cannon Smoke and carbon monoxide alarm Microwave Coffee and Tea Coffee maker/Kettle Fridge Toaster Cooking utensils Games Binoculars (stays on property) Fresh linens provided Toiletries Body wash, shampoo, conditioner Water heater(6 Gallon) Tv (with streaming apps)
Pets
Potable water
Toilets
from 
$100
 / night
Hudson Getaways @ Leeds, NY

19. Hudson Getaways @ Leeds, NY

83%
(3)
46mi from Winchester Center · 5 sites · Lodging · Catskill, NY
Two hours from NYC, close to skiing (hunter mountain/ Windham , Kaaterskill falls, Woodstock, Hudson, Saugerties. FAQ Is my rental secluded? Our property is 8 acres, exactly the same as seven football fields. From your private deck and the big window, you will not see any other houses as far as eyes can see. We added fence panels to make it even more private. We have attached a satellite picture of the property to give you a better idea. As required by zoning law, there is a larger cabin on the property. But it is far enough and visually isolated enough that you won't feel it's presence (at least from the feedback we got from other guests.) We are located in a rural hamlet and a mile down the road there is a tiny town with two cafes , two bars and two restaurants. But your place is one New York block distance away from the street towards tree filled uninhabited area, adding to the sense of seclusion. I have never been in a tiny house, what can I expect? The "tiny house nation" style tiny houses are around 144 to 250 sqft, ours is 144 sqft. So,we are on the "smaller" side. Our guests have commented that its actually does not feel cramped. You will have heating, AC, hot shower, flushing toilet, kitchenette for basic cooking, small fridge, queen bed etc. You also have a private deck and a private outdoor fireplace to make S'mores and to grill. Are pets allowed? We just require that they should never be left alone and peace pick up after them. Our cleaning company charges a pet fee. If you forgot to pay it or decided to bring a pet last minute, please leave the amount as a tip to the cleaners. That way the cleaners get to keep the money and then they won't report the pet to the cleaning company. This also saves us the hassle of going back and forth with the cleaning company, reviewing the camera footage and ultimately paying it out of our own pockets. Also, please keep in mind that the house is really small at 144 sqft which may be too cramped for some large dogs. I work from home, how is the WiFi? We have had multiple guests who worked from home during the pandemic. Our provider is spectrum (the monopoly in the area). Luckily, outages are very rare and get fixed promptly (you may have to restart the router). Speed is always good for multiple simultaneous video calls and movie streaming. Do you provide firewood? Not yet! You do not need firewood to heat the house. If you want to use the outdoor fireplace, look for 'Campwood' signs and buy from our neighbors.(Also @ Walmart, Stewart gas stations etc.) What about Towels-Soap-Linens-Hot water? Is there heating/cooling? Can we cook? Yes! Yes! Yes! and Yes!. Think of all the amenities a hotel provides plus a tiny kitchen. Hot plate, refrigerator, electric kettle, drip coffee, plates, cutlery - we have all that we could cram into the tiny space. Our guests use the outdoor fireplace for BBQ and smores! Can I check in early? or Check out late? No and Yes. Due to the super strict covid19 cleaning process, we can no longer offer early check in. However, we can offer late checkout up to an hour. Please inform us in advance so that the cleaning crew can adjust accordingly.
Pets
Potable water
Toilets
from 
$24
 / night
Spacious Skies Woodland Hills

20. Spacious Skies Woodland Hills

94%
(41)
35mi from Winchester Center · 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*
Pets
Potable water
Toilets
from 
$40
 / night
95% (1.9K)

Top-rated campgrounds

Humble Farm with Simplicity

1. Humble Farm with Simplicity

96%
(212)
44mi from Winchester Center · 10 sites · Tents, RVs, Lodging · Higganum, CT
Bring your family and friends to camp at our quiet and very earthy and modest small family farm. Located in backwoods horse pastures with chickens, a dog, and a few horses. The property is very spread out and there are 2 outhouses for all sites to use. Your pets are welcome too! Locally there are state parks with beaches, and state forest for trails and lakes, hiking and biking. Or you can just relax and enjoy the serenity! OUR ADDRESS IS #200 NOT #204 Two parallel driveways THE DRIVEWAY TO THE LEFT FROM THE STREET IS OURS. Other attractions include local farmers markets, Millers Pond, Hammonassette State Park Beach, Gilette's Castle, with the famous River Ferry crossing the Connecticut River with a vehicle across to East Haddam at end of Rt. 148... We offer an hot H2O outdoor shower here for the comfort of out clients. It is located on the back of main house in corner. Entrance through gate is marked. Also See map in photos. We cannot allow any wood for camp fires to be brought in form the outside for environmental reasons. It can be pre-purchased for $12 per bundle on this site, or $10.00 cash here at farm. Farm Fresh eggs daily when available for $5.00 per 1/2 dozen. Blankets and pillows only are provided, NO LINENS for cabin or trailer sites only. Garbage removal is available as well $5 per bag provided.
Pets
Potable water
Toilets
from 
$49
 / night
two story tiny cabin with two windows on bottom floor and two screened windows on top floor that can open

2. Atland Artist Residency

100%
(110)
37mi from Winchester Center · 9 sites · Tents, Lodging · West Chesterfield, MA
We're named one of the best Hipcamps to visit in 2024 and 2023! Over 40 acres of solitude tucked in the hilltowns of the western Massachusetts Berkshires -- boasting warm sunrises over the distant hills, lush forest for hiking and meandering river frontage on Bronson Brook and walking distance to the Westfield River to wade and soak in the cool mountain water or fish for native trout! The cabin and camping sites are located in beautiful trails that were created around the main home -- an architect designed masterpiece boasting a wonderful asian influence yet handcrafted from the very timberstock off the land on which it sits lending a refined rustic twist. 25 Min to Northampton and 10 min to the Berkshires! You can hike or bike to the best swimming holes around and camp within our beautiful forested hills of hemlock, birch, maple, and wildflower meadow. If you're into kayaking/canoeing/tubing/hiking/fishing, then this is the perfect space for you. Come escape and breathe in our cool clean mountain air :)
Pets
Potable water
Toilets
from 
$45
 / night
Woodland's Edge Glamping & Hot Tubs

3. Woodland's Edge Glamping & Hot Tubs

90%
(109)
46mi from Winchester Center · 3 sites · Lodging · Belchertown, MA
Choose between our extra large tent can hold a family/friend group of up to 8 comfortably, but is also cozy enough for a couple's getaway. Or our sweet-as-can-be tiny A-frame cabin. Our private site is in the middle of a mixed-wood forest. Deer roam free and you will surely hear the call of coyotes and owls at night. Centrally located within 10 minutes of downtown Amherst, 15 minutes to downtown Northampton, this tent is the perfect base camp to access all that this region has to offer. Flea markets and farmers markets on the weekends, malls, museums and numerous restaurants in the area should you decide to venture out for a bite to eat. Holland Glen, a popular hiking spot with waterfalls and swimming holes is a quick 3-minute drive to the trail head. It is an easy 1-mile ride to the start of the Norwotuck Rail Trail a paved bike path through wetlands and rolling farmland. Or simply stay put, unplug, and relax in one of the hammocks or enjoy our one of a kind wood-fired hot tubs! Our guests are welcome to wander around our little homestead have your coffee in the pollinator patch and watch the hummingbirds, butterflies and bees do their thing. Feed the chickens, then nibble your way through our berry patches, fruit trees and gardens and experience what it is like to live simply in New England. Cook a meal over the fire - we will provide the cast iron pans and dishes if needed. Learn more about this land: A private campsite on the edge of a woodland forest. Deer roam free and you will surely hear the coyotes call at night. Centrally located within minutes of Amherst and Northampton, this tent is the perfect base camp to this vibrant region. Relax in the hammock with a good book, play a rowdy game of corn hole, sip your coffee in our pollinator patch, tell stories by the campfire or rent our projector for the night for a fun in-tent movie!
Potable water
Toilets
Campfires
from 
$77
 / night
Upper Shire Campsites Hudson Valley

7. Upper Shire Campsites Hudson Valley

100%
(238)
29mi from Winchester Center · 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)
Pets
Potable water
Toilets
from 
$90
 / night
Wyomanock Farm

8. Wyomanock Farm

97%
(844)
44mi from Winchester Center · 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.
Pets
Potable water
Toilets
from 
$32
 / night
The Awakening Garden

9. The Awakening Garden

100%
(10)
48mi from Winchester Center · 4 sites · Lodging · Saugerties, NY
This piece of land was developed by my mother, and named after my grandmother: The Awakening Garden is a translation of her name in Chinese. It is tucked in between the Hudson River (8 miles to the East) and the Catskill Mountains (10 miles to the west). It is just 6 miles from the Village of Saugerties and 14 miles to Woodstock, NY. The piece available for camping is 10 acres, but the entire Garden is comprised of 98 acres of rolling land (most of it in a forestry protection plan) bordered on the west by acres of marshland. Many trails criss-cross the Garden and lead one to pretty or interesting vistas including a large mountain laurel patch, ancient graveyard, and different stands of mixed wood forests. There’s lots of wildlife both on land and in the marshes.
Pets
Potable water
Toilets
from 
$93
 / night
Magical Yurt in the Woods

14. Magical Yurt in the Woods

100%
(5)
42mi from Winchester Center · 1 site · Lodging · Williamsburg, MA
A magical place in the woods inviting a return to your essential nature located amongst watershed land in Williamsburg, MA. Simple, quiet, and cozy. The space works in many wonderful ways, especially as a vessel for nurturing self-directed retreats like writing or meditation retreats. Many local trails including The Holyoke Range, The Berkshires Mountains, Graves Brothers Loop Trail, and Petticoat Hill Trail Loop. Experience nature, trails, starry nights, and hooting owls. The Yurt is located a twenty-minute drive from the vibrant downtown of Northampton, MA. The Yurt is a wonderful place for parents to stay when your kid graduates from one of the Five Colleges: Smith College, Amherst, Mt.Holyoke, Hampshire, and U. MASS. The Yurt is a short drive from MASS MoCA, Green River music festival, Tanglewood music festival, and Jacob’s Pillow. What have previous Yurtlings said about this space? "We came to celebrate a birthday and, within that, generate a shared transcendent experience. The yurt is the ideal container to hold such a ceremonial and sacred journey. The weekend was more than we could have hoped for! Thank you Carolyn! In Unity + Gratitude, Sara + Pete" "At night we heard barred owls calling out, it reminded that quiet isn't silent, and the darkness has layers, it is never just one thing. ❤️Cate and Em" We are extremely blessed to live in the woods amongst watershed land and hooting owls. With nothing but star-lit skies, I’m delighted to extend this sliver of natural beauty to you.
Potable water
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Showers
from 
$125
 / night
The trails through the forest offer a nice place to stroll.

15. Sunflower Retreat

99%
(103)
39mi from Winchester Center · 1 site · Lodging · Cummington, MA
A humble, 2-acre vegetarian family micro farm. Home to our family of five, 2 cats, 2 rabbits and nineteen chickens. Beautiful, established flower gardens, fruit trees and veggies. This is also home to Sunflower Yoga & Mindfulness where yoga and meditation are taught. The cabin is nestled in the 1 acre of woods behind our home, protected by large old pines and surrounding acres of forest. Home to many songbirds, woodpeckers, raven, deer, porcupine and the occasional black bear. A true retreat. Small, rustic cabin with electricity in the woods behind our home in the hilltowns of Western Massachusetts. You are just 300 feet from the house, but while in the woods you will have complete privacy. The woods are filled with songbirds and there is a small platform for meditation. There is no wifi in the cabin, so enjoy the ability to disconnect from it all while connecting within. The hilltown region is rich with rivers and lakes for swimming, boating and fishing and forests for hiking. We are just 30 min to Northampton and 45min-1hour from the many cultural offerings of the Berkshires.
Potable water
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$68
 / night
The full bathroom is on the back end of Howards house.

16. Sacred Hollow in Heart of Hudson

91%
(22)
49mi from Winchester Center · 4 sites · Tents, RVs, Lodging · Hurley, NY
the locals know our street because of the indigenous people and early Dutch settlers mixing with the slaves. Much history here, with the small town of stone houses, making Hurley a national historic destination. This serene is secluded on a mountain surrounded by trees with seasonal views. The campsite is neighboring 105 acres of beautiful conservatory land available for hiking. No true trails are available, but you can be adventurous and hike further up the mountain, arriving to a clearing, providing you with a lovely mountainous view. From the mountain, you can hike to a waterfall or even hike across a lovely plain field surrounded by mountain ranges on both sides and crossing the creek over to Historic Stone houses in Hurley. Within a 10 minute drive check out some of the local restaurants like Alebrijes, Hickory BBQ & Smokehouse, and the Hurley Inn where the movie “Tootsie” was filmed!. Hurley Marbletown Trailhead and Rail trail parking are only a 6 minute drive away! The town of Kingston is about 15 minutes from our site where you will find Bluestone Wild Forest, antique shops, restaurants, other outdoor activities! The nights are just spectacular as you look into the sky surrounded by a blanket of stars, able to see the many constellations looking like jewels on a black cloth. The sounds of nature and all of it's distinct calls including that of eagles, is truly an experience. And we cannot forget our other friendly neighbors, the wild turkeys and deer! We are very appreciative of this beauty and would love to share this sacred place with you. Learn more about this land: Feels like you’re away from civilization but yet close to all the Hudson valley has to offer. 15-20min from Woodstock, rosendale, stone ridge, Rhinebeck, red hook, New Paltz and Mohawnk short 30 min drive. The glampsite is a yurt with a fire pit and a full modern bathroom just a short walk away. For a small fee, you can also rent our bikes for riding the nearby rail trail or just visit the waterfall 2 miles away. Wood available for purchase. THE HOT TUB IS PART OF A MINI-SPA PACKAGE AAND IS AVAILABLE FOR AN ADDITIONAL FEE. Not only will You be relaxing, but also connecting with the cosmos through a 1 hr transformative healing session offered by the host for an extra fee.
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from 
$54
 / night
Quentins Treehouse

17. Quentins Treehouse

97%
(158)
19mi from Winchester Center · 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
The Catskill And Chill

18. The Catskill And Chill

95%
(38)
46mi from Winchester Center · 1 site · Lodging · Catskill, NY
Located In upstate New York is this hidden gem. This camper was old school, now turned new. With a full renovation to give it a Scandinavian look in the front, and a cozy cabin feel in the bedroom. This will give you a unique experience different from the normal camper your used to! Also at your campsite there is a firepit, garden hose,(not available during the winter)and a 8x8 hammock perfect to stargaze in! We are now offering kindling firewood with fire starter and matches. Feel free to reserve your own firewood. $10 *PLEASE READ THIS BEFORE BOOKING* I want to be transparent with you guys on the property and size of the camper! -The camper is very small only 21ft. The average height clearance is 6'2" so if you are tall this may not be for you. (I'm 5'9" and its comfortable for me) -If you are a bigger person this may feel too tight for you especially in the bathroom area -The bed is a full size some couples may feel that this is to small for them. -A hot shower will last about 15 minutes once it is heated up. -In the summertime there is bugs some may get into the camper. We do treat the area with safe bug spray but it may not fully prevent them. -There are two other tiny houses and a main house on the property. They are far apart but the main house is close. We have a privacy fence that fully blocks the house. So you are still very private but you are not fully secluded. -In case of fire There is a fire blanket, fire extinguisher, and a smoke/carbon monoxide detector inside the camper. The bedroom door is only to be used as an emergency fire exit. (Door is locked from the outside but unlocked from the inside) There is also a water cannon outside for outdoor fires. Please be responsible with all fires! -If you want to cancel you must cancel within 24 hours of booking then I will issue a full refund. Any time after that its a strict policy and no refund will be issued. Thank you for reading this I want to make sure everyone is aware and knows what to expect. Its still an awesome place and people love it! Hope this helps! OTHER AMMENDITIES INCLUDED: Bottled water Wifi Heating Air conditioning Fan and air purifier First Aid kit Fire extinguisher, fire blanket, water cannon Smoke and carbon monoxide alarm Microwave Coffee and Tea Coffee maker/Kettle Fridge Toaster Cooking utensils Games Binoculars (stays on property) Fresh linens provided Toiletries Body wash, shampoo, conditioner Water heater(6 Gallon) Tv (with streaming apps)
Pets
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from 
$100
 / night
Hudson Getaways @ Leeds, NY

19. Hudson Getaways @ Leeds, NY

83%
(3)
46mi from Winchester Center · 5 sites · Lodging · Catskill, NY
Two hours from NYC, close to skiing (hunter mountain/ Windham , Kaaterskill falls, Woodstock, Hudson, Saugerties. FAQ Is my rental secluded? Our property is 8 acres, exactly the same as seven football fields. From your private deck and the big window, you will not see any other houses as far as eyes can see. We added fence panels to make it even more private. We have attached a satellite picture of the property to give you a better idea. As required by zoning law, there is a larger cabin on the property. But it is far enough and visually isolated enough that you won't feel it's presence (at least from the feedback we got from other guests.) We are located in a rural hamlet and a mile down the road there is a tiny town with two cafes , two bars and two restaurants. But your place is one New York block distance away from the street towards tree filled uninhabited area, adding to the sense of seclusion. I have never been in a tiny house, what can I expect? The "tiny house nation" style tiny houses are around 144 to 250 sqft, ours is 144 sqft. So,we are on the "smaller" side. Our guests have commented that its actually does not feel cramped. You will have heating, AC, hot shower, flushing toilet, kitchenette for basic cooking, small fridge, queen bed etc. You also have a private deck and a private outdoor fireplace to make S'mores and to grill. Are pets allowed? We just require that they should never be left alone and peace pick up after them. Our cleaning company charges a pet fee. If you forgot to pay it or decided to bring a pet last minute, please leave the amount as a tip to the cleaners. That way the cleaners get to keep the money and then they won't report the pet to the cleaning company. This also saves us the hassle of going back and forth with the cleaning company, reviewing the camera footage and ultimately paying it out of our own pockets. Also, please keep in mind that the house is really small at 144 sqft which may be too cramped for some large dogs. I work from home, how is the WiFi? We have had multiple guests who worked from home during the pandemic. Our provider is spectrum (the monopoly in the area). Luckily, outages are very rare and get fixed promptly (you may have to restart the router). Speed is always good for multiple simultaneous video calls and movie streaming. Do you provide firewood? Not yet! You do not need firewood to heat the house. If you want to use the outdoor fireplace, look for 'Campwood' signs and buy from our neighbors.(Also @ Walmart, Stewart gas stations etc.) What about Towels-Soap-Linens-Hot water? Is there heating/cooling? Can we cook? Yes! Yes! Yes! and Yes!. Think of all the amenities a hotel provides plus a tiny kitchen. Hot plate, refrigerator, electric kettle, drip coffee, plates, cutlery - we have all that we could cram into the tiny space. Our guests use the outdoor fireplace for BBQ and smores! Can I check in early? or Check out late? No and Yes. Due to the super strict covid19 cleaning process, we can no longer offer early check in. However, we can offer late checkout up to an hour. Please inform us in advance so that the cleaning crew can adjust accordingly.
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from 
$24
 / night
Spacious Skies Woodland Hills

20. Spacious Skies Woodland Hills

94%
(41)
35mi from Winchester Center · 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*
Pets
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Toilets
from 
$40
 / night

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