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Upper Shire Campsites Hudson Valley

Hosted by Joanna · Hillsdale, New York
6 sites · RV, Tent, Lodging · 22 acres
100%
·
211 reviews
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Best Hipcamps in New York
Named one of the best Hipcamps to visit in 2025.
Family-friendly
Recent Hipcampers say this Hipcamp is great for families and kids.
Best in New York: Finalist
Named one of the best Hipcamps to visit in 2024.
Joanna K. is a Star Host
Star Hosts are highly rated, responsive, and committed to providing incredible experiences.
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)

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RV/tent sites

2 sites
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Upper Shire Meadow

99%
(91)
RV/tent site · Sleeps 6 · Vehicles under 25 ft
Park your rig or pitch your tents at the top of our gorgeous hill and enjoy the 360-degree views and the breezes. This site comes with 4 acres of roaming/trails, a fire pit, Adirondack chairs, hammocks and, solar-powered string lights. Best bird watching happens here. Book your stay at this campsite as it is our most popular. If your group exceeds six people please message us about our additional guest fees ($25 a night per person). Extra easy pop-up two-person tents are available to rent ($15 for two nights.) As of July 2024 we have opened a brand new (two) Shower Shack with hot and cold water.
Short walk to site
4WD recommended
Campfires allowed
Toilet
Potable water
Pets allowed
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The Entire Upper Shire Campground

100%
(2)
RV/tent site · Sleeps 25 · Vehicles under 25 ft
PLEASE NOTE, this site books out the entire property! You will have access to the airstream, a-frame cabin, bell tent and RV/tents sites. For weekends this is a two night minimum stay rental. We can accommodate up to 30 guests in total. For the tent/RV sites, you must bring your own camping gear. As of July 2024 we have opened our brand new (two) Shower Shack with hot and cold water. Please read each of the site descriptions to understand what is included in your stay. Pets are allowed but they must be kept on leash. Potable water available. Portable toilets available onsite. 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. Located in Columbia County near the border of Massachusetts and New York. 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. This place comes with a relaxed atmosphere and is located near Catamount Ski Resort, Bash Bish Falls, Taconic State Park, Hudson NY, and Great Barrington, MA.
4WD recommended
Campfires allowed
Toilet
Potable water
Pets allowed
No electrical hookup

Lodging

4 sites
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Pine Grove Bell Tent

100%
(36)
Bell tent · Sleeps 3 · 1 bedroom · 2 beds · 1 toilet
A 13-ft diameter White Duck Bell Tent on a custom-built tent platform in a Pine Grove next to a shady pond. We've included a campfire ring with a grill, solar-powered string lights, Adirondack chairs, and campfire blankets. Our Bell tent is outfitted with a small Jackery power station, one queen-sized air mattress, and a sleeping cot with a Japanese futon. Hillsdale, NY has a brewery, cidery, the longest Zipline in North America and so much great hiking nearby. If you have friends that would like to join you with their own tents on this site that can be arranged for an extra fee. The Taconic State Park is close by for hiking and kayaking as well as Guilder Pond in Mt. Washington, MA. The towns of Great Barrington, Ma. and Hudson, NY both a short drive away. So much to explore, see, and do in this area nestled in the eastern corner of the Hudson Valley next to the Berkshires. If you plan on bringing a pet to the Bell Tent please be sure to add that fee to your booking under "extras" ($25) If you have an additional guest(s) that want to pitch a tent on the the Bell Tent campsite that fee is ($25 a night per person) and you will need to message us on how to arrange that. We have a few new easy pop-up two person tents that are available to rent ($15 for two nights) you can also find that option under extras along with bundles of firewood for ($15)
Campfires allowed
Toilet
Potable water
Pets allowed
Showers
No picnic table
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Instant book

Off Grid A-Frame Cabin by The Pond

100%
(34)
A-frame · Sleeps 3 · 2 beds
This newly constructed 3-season A-Frame sleeps up to 3 adults or two adults and two small children. This pine and cedar cabin is furnished with a queen-sized bed, a full-sized futon couch (to be used with your own sleeping bag and pillow) reading lights, and jute rugs. Deck furniture is a set of chairs with a small end table for morning coffee or a nightcap. Power for lights, music, a tea kettle, a PC, and a fan is made possible with the use of a Jackery power station. A fire pit and two Adirondack chairs will be set out front for use by guests at this site. An outhouse and parking is nearby for use by guests. It’s truly a hideaway nestled in a pine grove in front of a picturesque pond in the Hudson Valley very close to the Berkshires. The sliding glass doors with a screen plus a picture window with a screen make this A-frame well-ventilated for summer stays. The cedar live edge privacy screen completes this campsite on private land in a very bucolic setting. A brand new propane heater/fireplace has been added to this cabin recently for colder nights. If this Aframe is booked for the dates you want to visit please take a look at our new Black and Tan Pondside Log Cabin at Upper Shire Hudson Valley NY. (On HipCamp) 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 want to pitch a tent in front of the cabin 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 are available to rent ($15 for two nights) you can also find that option under "extras" along with bundles of firewood ($15)
4WD recommended
Campfires allowed
Toilet
Potable water
Pets allowed
Showers
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Instant book

1987 Airstream at Tin Can Valley

100%
(27)
Airstream · Sleeps 4 · 2 bedrooms · 3 beds
Enjoy the unmistakable vibe of a vintage Airstream trailer in our newly-refurbished 1987 Sovereign 27, which sleeps 4 with a super comfy queen bed area beneath the panoramic windows up front and 2 mid-cabin twin-sized bunks. The trailer is sited on a very private, gently-sloped acre of cleared lawn and meadow flowers tucked between a pine grove and deeper woods, within the Upper Shire campground in eastern Columbia County of New York's Hudson Valley. As of July 2024 we have opened a brand new (two) Shower Shack with hot and cold water. The trailer has off-grid solar panels powering the cabin lights and stereo, and we have provided a Bluetti solar generator for your 120v needs. There is no wifi, but the cell coverage is excellent for both major carriers. The kitchenette has an electric kettle and a French press for your morning coffee. There is no running water currently on the property, so the trailer is dry-docked, but we can provide potable water upon request, and there is a clean porta-potty (serviced weekly) located nearby. Outside the trailer, the site is equipped with 2 Adirondack chairs around a metal fire ring a grilling grate, a small table, and 2 hammocks for total relaxation. Firewood is available for purchase; NYS regulations prohibit the importation of out-of-state wood (or wood sourced more than 50 miles from the Upper Shire campsites) that isn't heat-treated to prevent the spread of evasive pests. The Upper Shire Campsites are dog-friendly; leashed, well-behaved pups are always welcome! Our campsites have a leave-no-trace carry-in carry-out trash policy. Please take everything you bring in back out with you. If you plan on bringing a pet to the Airstream please be sure to add that fee to your booking under "extras" ($25) If you have an additional guest(s) that want to pitch a tent in front of the Airstream that fee is ($25 a night per person) and you will need to message us prior on how to arrange that. We have a few easy pop-up two-person tents that are available to rent ($15 for two nights) you can also find that option under extras along with bundles of firewood for ($15)
4WD recommended
Campfires allowed
Toilet
Potable water
Pets allowed
Showers
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Instant book

Black & Tan Cabin at Pondside

100%
(7)
Cabin · Sleeps 4 · 1 bedroom · 2 beds · 1 toilet
This authentic (off grid) log cabin is now available for your camping adventures! We are so excited to add this pondside cabin to our campsites. It will sleep a family of 4 (with two small children) or 3 adults depending on the age(s) of the members of your group. We will take bookings now starting now. This modern Black and Tan hand-peeled pine log cabin has six operating windows, front door, a queen sized bed and a full sized sleeper sofa/futon. Windows that look out to the pond, a porch to relax on in a rocker, a fire pit, and hammocks. To get an idea of the inside amenities (a Jackery power source, a tea kettle, lighting and furniture) please see our listing for our A-frame cabin. Have any questions please feel free to contact us and we will get right back to you.
Campfires allowed
Toilet
Potable water
Pets allowed
Showers
No picnic table

Reviews

100% Recommend253 ratings · 211 reviews
Recommends
· July 2026
Hot showers + camping
20 ft truck camper · With pets ·
Upper Shire Meadow
Great spot! Joanna has great signage making it easy to navigate. The showers were a huge bonus during the summer!
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Kristin S.
15 reviews
Recommends
· June 2026
Lovely A-Frame
Off Grid A-Frame Cabin by The Pond
Beautiful structure that has everything you really need for basics. Cozy even in the rain. Best outdoor shower I’ve ever had! We would love to return and highly recommend. One note, if you are looking to swim or paddle board in the pond on property keep looking. It’s nice for a short canoe and that’s about it.
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Emily F.
6 reviews
Recommends
· June 2026
Five Star Rating !
With kids ·
Black & Tan Cabin at Pondside
We loved our stay at the Upper Shire campsite. We stayed in the black and tan cabin, which was amazing. The bed was really comfortable. Joanna was very helpful and always quickly responded to messages. Would love to go back!
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Joanna N.
3 years on Hipcamp
Recommends
· June 2026
With kids ·
1987 Airstream at Tin Can Valley
Excellent campground, super-friendly host and the location is lush and quiet. Cannot wait to go back!
A
Alex V.
2 reviews
Recommends
· June 2026
Best camping trip ever!
Pine Grove Bell Tent
One word, magical. The grounds are so beautiful and private. We had such a great time. Joanna is wonderful, so accomidating and engaging. She set us up for one of the best camping trips we have ever experienced. We will definitely be back.
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Brian M.
1 month on Hipcamp
Recommends
· June 2026
don’t sleep on the shire
10 ft travel trailer ·
Upper Shire Meadow
Wow, killer site and amazing hosts !! The site was clean, well maintained, the best views, private and well marked ! Hope to come back to the shire again soon, thanks guys
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Val F.
9 reviews
Recommends
· June 2026
16 ft car ·
Upper Shire Meadow
Me and my wife have been camping in a lot of places upstate and this was by far the best. Joanna’s property is gorgeous and extremely quite and she has been an absolute star in communicating with us, welcoming us and providing us with fire and water. Absolutely recommended! Cant wait to be back.
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Nicholas S.
3 years on Hipcamp
Recommends
· June 2026
Tent ·
Upper Shire Meadow
Well kept grounds with about 50 yards between sites. Great showers that are hot. Joanna brought us water everyday, which is really convenient.
J
Justin L.
3 months on Hipcamp
Recommends
· May 2026
Best campsite
Pine Grove Bell Tent
We really like this campsite. My wife enjoy everything . We will back soon. Joanna was very friendly she help us a lot. Thank u joanna.
J
Julio D.
1 year on Hipcamp
Recommends
· May 2026
Awesome place
Tent ·
Upper Shire Meadow
Amazing site, great location, so quiet and lovely. Joanna was an amazing host.
B
Brontë E.
2 reviews
Recommends
· May 2026
With pets ·
Off Grid A-Frame Cabin by The Pond
We had a great stay in Joanna’s A-Frame cabin! The cabin overlooks the pond which you can see from inside, cooking around the campfire and from the water in the canoe that’s located onsite. There are thoughtful amenities like hot outdoor showers, a double sleeping bag and French press that made our stay that much more enjoyable. The firewood we purchased was good sized and dry! The property is beautiful with trails throughout. It’s a great place to stay for a relaxing weekend away! We’ll definitely be back :)
N
Nicole L.
3 months on Hipcamp
Recommends
· November 2025
Off Grid A-Frame Cabin by The Pond
Amazing stay! Host was really helpful and campsite is well kept
J
Jarvis S.
9 months on Hipcamp
Recommends
· October 2025
With pets ·
Pine Grove Bell Tent
Would go again! Great location, accommodating hostess
S
Shane R.
10 months on Hipcamp
Recommends
· October 2025
Group trip ·
1987 Airstream at Tin Can Valley
Our time at Tin Valley in Upper Shire Campground was so special. Joanna’s land was beautifully maintained and the campsite had everything we needed and more - a fire pit, hammocks, comfortable beds to lay in, even an electric kettle and french press! The outhouse was a very convenient location and warm showers was a huge plus - made the weekend a perfect glamping excursion. Location was lovely as well, just a short drive from fantastic hikes like Bash Bish Falls and Little Apple Cidery, where we had a great time at the Orchard Bar. This was my first adventure through HipCamp and Joanna made it an easy and perfect experience - thank you!
S
Sindu S.
10 months on Hipcamp
Recommends
· October 2025
Amazing weekend!!
Off Grid A-Frame Cabin by The Pond
Joanna was a great host and the site was perfect!!!
T
Tien T.
1 year on Hipcamp
Recommends
· September 2025
With kids ·
Black & Tan Cabin at Pondside
Great stay with Joanna at the little log cabin. Beautiful property and fun downtown area in Hillsdale. Family enjoyed it very much and hope to return again. Peaceful and unplugged.
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Shea B.
2 reviews
Recommends
· September 2025
Pine Grove Bell Tent
Truly a fantastic experience. Owner was extremely attentive. Best part- the showers!! Beautiful, well maintained, and piping hot water at any time of day/night. Absolutely recommend! 10/10
A
Ashley L.
2 reviews
Recommends
· September 2025
Excellent campsite!
With pets ·
Off Grid A-Frame Cabin by The Pond
The campsite was wonderful! We stayed at the A frame cabin which was right on the pond. Everything was well maintained and we had a blast. Hoping to go again and bring some friends next time.
M
Michael K.
1 year on Hipcamp
Recommends
· September 2025
Beautiful and Private
1987 Airstream at Tin Can Valley
We had a fabulous weekend on and off the site. The site itself is beautiful and simple, with everything you could need. There were other campers but it felt totally private. The Airstream itself is so cute, and the bed was super comfortable. The shower is GREAT, plenty of hot water. We blew through our wood the first night (stargazing was spectacular) and Joanna delivered more for us the next morning. We did a ton of little activities nearby, guided by Joanna's helpful list. We'll definitely be back.
C
Carolyn O.
1 year on Hipcamp
Recommends
· August 2025
17 ft travel trailer ·
Upper Shire Meadow
Wonderful to stay at Joanna's place again to watch the Perseid shower. Joanna does a wonderful job maintaining these spaces and we're happy to have visited for a second time. Seamless communication and lovely site. Thanks so much!
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Shey R.
5 years on Hipcamp
Recommends
· August 2025
Camping in Hillsdale, NY
Pine Grove Bell Tent
We spent two nights at Joanna’s campsite and really liked everything about it. Despite arriving late, we were greeted. Joanna has been helpful throughout, answering our questions real-time during our stay. Her recommendations of local sites helped us save time and enjoy highlights. The outdoor showers were first in class. Thanks
M
Markus F.
2 reviews
Recommends
· August 2025
Pine Grove Bell Tent
Camp grounds are in excellent condition. Lots of space and privacy. Showers also in excellent condition. Short drive to town for supplies and plenty of hiking options nearby. We had a great time. Joanna’s hospitality is second to none. Looking forward to our next trip.
C
Ciaran M.
11 months on Hipcamp
Recommends
· August 2025
Fantastic for Adults, kid & dogs
With pets ·
Black & Tan Cabin at Pondside
The Black & Tan cabin was great for us. For 2 adults, a 1.5 yr old and 2 dogs. It was secluded, had great area for playing, grilling and hanging by the fire. It had just enough features for staying plugged in but you could be completely off the grid if you want. I loved the bed, futon can be stiff (wife liked it). The cabin has big windows which got all the fresh air in at night. Best sleep we’ve all had in a while. My only recommendation would be to add one of those magnetic screens for the front door to keep that open all day without the flys getting in. The shower shack was also great. If you want complete seclusion this place is great cause we knew other people were on property but it never was an issue, didn’t see or hear them once in our area. We’ll be coming back for sure.
C
Cody C.
11 months on Hipcamp
Recommends
· August 2025
Airstream
Group trip ·
1987 Airstream at Tin Can Valley
Nice campsite - cool camper - close enough to amenities but private enough as well. I would stay again
L
Logan M.
1 year on Hipcamp
Recommends
· August 2025
Tent · Group trip ·
Upper Shire Meadow
My family and I (5 adults) enjoyed staying at Joanna's camping site - it was quiet, beautiful, and clean, with a really lovely outdoor shower and some extra touches like string lights and a couple hammocks at our site. Joanna was quick to respond to messages and flexible with some slight, unexpected changes on our end. It was also close to some lovely places to check out like Copake Falls swim area, a little cidery down the road, and not too far from other towns like Stockbridge for other activities.
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Talia G.
4 reviews
Recommends
· August 2025
Tent · With pets ·
Upper Shire Meadow
We had perfect weather for this weekend of tent camping in Joanna’s meadow. Close to Taconic State Park, Great Barrington, and the Harlem Valley Rail Trail - lots to do around the area. Campsite felt quiet and private even though there were a few other locations on the property. Couple considerations: you are fairly close to route 22 and the noise from the road carries, but didn’t notice it at all overnight. Our dog picked up quite a few ticks brushing up against the long grass and brush around the meadow - so make sure you do your tick checks after staying!
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Harry I.
3 reviews
Recommends
· August 2025
15 ft pop-up camper · With pets ·
Upper Shire Meadow
This was my second time returning to the Upper Shire Campsites, and I'll definitely be back. I can say enough good things about the sites, the host, and the experience. First, each site feels private and secluded, even when other people are on the land. Second, the well-maintained trails offer plenty to explore. Third, the shower house is a fantastic luxury to have when camping, in addition to the portapotties. Beyond the great spot, the location itself is well-situated for exploring the Berkshires. Great Barrington is a quick drive, and Hillsdale is fun to explore as well. I spent a week camping there, and it was great enjoying the land and the host's hospitality.
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Max E.
17 reviews
Recommends
· August 2025
With kids ·
1987 Airstream at Tin Can Valley
Beautiful, near all the right spots and exactly what we were looking for. Hope to go back!
M
Miquela C.
1 year on Hipcamp
Recommends
· August 2025
Tent · Group trip ·
The Entire Upper Shire Campground
The perfect setting for either an intimate getaway or a family filled adventure. Had so much fun celebrating my 50th birthday there with family and friends.
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Leilani B.
1 year on Hipcamp
Recommends
· July 2025
3rd Timer!
Tent ·
Upper Shire Meadow
3rd time camping at Upper Shire. Absolutely love it. So peaceful and quiet. Love the outdoor showers. Close to Hudson for dinners but you have to go to Hy’s Fried Chicken which is 7 minutes away. Will def be back. Thank you Joanna!
B
Billy E.
2 reviews

Location

Hillsdale, Columbia, New York, United StatesTo respect the Host's privacy, the precise address of this land will be provided after booking
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Hosted by Joanna K. V.

Joined in April 2022
Response rate: 100%Response time: Within 5 hours

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