
House vacation rentals in Great Barrington
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Top-rated house rentals in Great Barrington
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Great Barrington house rentals
House rentals with free parking

The Berkshires Mountain Terrace LUX Home Sleeps 7
This was a beautiful and well kept home and was a delight to stay in. Natalia was also a lovely and communicative host. We had no issues and would happily stay there again.

Modern, cozy log cabin in Copake
Our stay at Julia's home was perfect! We all felt right at home, our grand daughter had lots of books, which she loves and other kids toys. The log cabin was more beautiful than pictured and the claw foot tub in the upstairs suite was the icing on the cake.

Pied-A-Terre | City of Hudson Entire Apartment
A wonderful host with a wonderful home. We enjoyed our stay so much that we are already planning another trip back. Highly Recommend!

Albany 2 Bedroom House
This was the first Airbnb I ever stayed at, and it was absolutely amazing! it was very clean and we really enjoyed our stay here. It is a nice safe neighborhood and area. if we ever came back out that way, we would definitely stay here again. this was the ideal home. Very cute & convenient set up

Hudson New York Grey Victorian
This house was perfect for our girls’ weekend in Hudson! It was spacious, clean, and had so much character. The location was great—just a short 5-minute drive to Warren Street. We didn’t walk due to the cold weather but it was definitely close and convenient. Would definitely stay here again!

Chatham Vilg Walk to Main. 100% Stocked/ SmokeFree
My mom and I had a wonderful stay at Uzziel’s place in Chatham! The house had everything we needed and was so close to the Main Street. Uzziel provided essentials and extras to make our stay comfortable and relaxing! ☺️ would definitely come visit again!!

Catskill Lumber House "Blue" - In Catskill Village
truly wonderful and considerate hosts! absolutely a wonderful stay and will 100% be back next time we are in town!

The Gatehouse at Raspberry Ridge
If your looking for a great quiet stay while visiting Hudson or other local places this home is it. Very clean, super dog friendly. Close to the highways and hidden enough to really be apart of nature.
House rentals with a hot tub

Modern Home in Woods w/ Hot Tub 10 Miles to Hudson
A beautiful, cozy, very well-stocked home. Remote enough to feel like you're in the country but in proximity to so many great activities on offer in Copake and Hudson. A special place. We had a wonderful stay.

Rhinebeck Home with an amazing outdoor space+H/tub
Michael and Enrique were excellent hosts, and left me and my girlfriends ice cream in the freezer to enjoy! They responded quickly when we had any questions. The view from the hottub looking out onto the woods is beautiful and the hottub was just what we needed to relax. A beautiful, cozy getaway, and so close to Rhinebeck!

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Lovely place to stay. Close to Hudson, but far enough to feel secluded.

Peaceful Hudson Valley Retreat House with HOT TUB!
Great spot to gather with friends. So close to trails and lovely towns. Loved the wood stove and hot tub!

Norbrook Farm ~ Rustic farmhouse w/ pond & trails
This is at least our 4th time staying at what we call "The Farm" and it is our favorite getaway! We even got my brother to drive 1.5 hours out of his way on his family trip to Boston so he could check it out. A rare gem!

Wooded Retreat w/ Hot Tub and Trout River
We really can’t say enough about Jackie’s place. Beautiful and peaceful surroundings. The home is well appointed and comfortable. The place is so nice we actually cancelled our plans for Saturday night just to stay in and enjoy the vibe. Spent part of the evening just relaxing in the hot tub looking at the amazing night sky!! The kitchen had everything we needed to cook dinner and a nice selection of pots and pans. Would highly recommend. Jackie was very responsive and easy to reach.

Elegant Year-Round Lakeside Retreat with AC
For our fourth stay at Katie and Greg's, we were just as satisfied as the first x3 trips! And we're already planning our 5th! Truly a gem of a home and wonderful hosts. Highly recommend!

Best of the Berkshires + Hot Tub by Evergreen Home
A truly cozy and thoughtful retreat. This house anticipated every need. The host created such a welcoming, hygge vibe—perfect for relaxation and feeling at home. I felt truly taken care of during my stay. A peaceful, well-thought-out getaway. (The vinyl ready to go was a lovely detail.)
House rentals with a pool

Charming lakeside cabin with private heated pool
My family and I stayed for a long weekend and were so glad that we did! It’s a beautiful cabin, with all the things you need. Kitchen is stocked with essentials, enough bathrooms, beds are super comfortable, hooks to actually hang things like towels, jackets… but we loved the outdoors even more! We walked to the lake, spent way too many hours in the pool, grilled, lounged, made s’mores by the fire pit and watched the beautiful stars at night. Couldn’t ask for more. Paula and her lovely family are SO welcoming it’s crazy. 😂. Hope to be back next summer!

Columbia County Farmhouse with Pool
Beautiful house with lots of beds and spaces to hang out. We had a lovely time here visiting the Hudson Valley in the early spring. Would certainly come back!

The Round House w/ Heated Pool
An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.

Modern Barn on 12 acres w Sauna, FirePit+swimming
there was lots to do inside the house as well as outside. everything was amazing

Farmhouse and Guesthouse w Pool, Pond and Sauna!
Donna was an amazing host and extremely responsive. The property was beautiful and exactly as described in the listing. The pool, pond, sauna’s made the entire experience feel like a special escape from the city. I highly recommend this property and can’t wait to go back!

10 Acre Country Estate with Pool, Hot Tub & Views!
We loved staying here with our family. It worked out perfectly having our daughter’s family on the one side of the house so if the baby cried it wouldn’t wake anyone up. A pack and play was also provided by Justin so we had a place for the baby downstairs as well. The house was roomy and comfortable for everyone. The hot tub wasn’t working right away but they let us know and had it fixed so we were able to use it during our trip. We would definitely stay here again and try it in warmer weather so we could use the pool as well. Thank you for a wonderful place to stay

Peaceful and Private Setting
I have nothing but wonderful things to say about Teva and his lovely home. The house is spacious, tidy, comfortable, and the surroundings are beautiful and peaceful. The beds were comfortable and everything you would need is there. We skied at Catamount which was ~20 minutes away - super convenient. Finally, and most notable, the overall experience and Teva’s attention to his guests’ experience was outstanding. He promptly and proactively reached out with local recommendations, was accessible during our stay for any questions, and made us feel right at home. We hope to come back over the summer for a little getaway.

Family home in the country
We loved staying at Craig’s house. Very warm and inviting with everything you need. Very quiet and peaceful wooded area which we enjoyed very much at the end of the day.
Quick stats about house rentals in Great Barrington
Total rentals
150 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
4.6K reviews
Family-friendly rentals
130 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
10 properties have a pool
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- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Six Flags New England
- Taconic State Park
- Thunder Ridge Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- Opus 40
- John Boyd Thacher State Park
- Mount Greylock Ski Club
- Hartford Golf Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Mount Southington Ski Area
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Beartown State Forest
- Otis Ridge
- Norman Rockwell Museum
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