House vacation rentals in Great Barrington

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Popular amenities for Great Barrington house rentals

House rentals with free parking

Top guest favorite
The exterior of the home is presented, showcasing a modern two-story structure. Lush landscaping features vibrant azaleas in purple and pink, with well-maintained shrubs bordering a gravel driveway. A garage is attached to the house, complemented by a serene backdrop of greenery.
Home in Egremont
4.96 out of 5 average rating, 120 reviews

The Berkshires Mountain Terrace LUX Home Sleeps 7

CourtneyRating, 5 stars2 months ago
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.
Guest favorite
A spacious outdoor deck features weathered wooden planks and two bright red Adirondack chairs facing the tranquil lake. Soft morning light illuminates the scene, while lanterns are placed along the railing, suggesting a serene spot for relaxation.
Home in Copake
4.9 out of 5 average rating, 134 reviews

Modern, cozy log cabin in Copake

JayRating, 5 stars1 month ago
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.
Guest favorite
A cozy living area is presented with a green couch positioned in front of a rustic wooden coffee table. A small blue vase holds fresh flowers, while magazines and a candle adorn the table, inviting relaxation and comfort.
Home in Hudson
4.86 out of 5 average rating, 458 reviews

Pied-A-Terre | City of Hudson Entire Apartment

MichaelRating, 5 stars1 month ago
A wonderful host with a wonderful home. We enjoyed our stay so much that we are already planning another trip back. Highly Recommend!
Guest favorite
The exterior of a ranch-style home is viewed from the front yard, featuring a simple design with a single-car garage. A paved driveway leads to the entrance, framed by a green lawn scattered with fallen leaves. A tree offers shade near the residence.
Home in Albany
4.8 out of 5 average rating, 10 reviews

Albany 2 Bedroom House

AlishaRating, 5 stars2 weeks ago
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
Guest favorite
A spacious living area is highlighted by two large artworks: a framed image of a person holding oranges and a striking mural featuring two figures near a vintage train. The warm wooden floors add a sense of openness to the room.
Home in Hudson
4.92 out of 5 average rating, 202 reviews

Hudson New York Grey Victorian

KarlaRating, 5 stars2 months ago
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!
Guest favorite
A comfortable living area is featured with a soft beige couch adorned with colorful throw pillows, complemented by a cozy armchair. A wooden coffee table sits at the center. Natural light filters through sheer curtains, enhancing the inviting ambiance.
Home in Chatham
4.9 out of 5 average rating, 181 reviews

Chatham Vilg Walk to Main. 100% Stocked/ SmokeFree

KeriRating, 5 stars1 week ago
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!!
Superhost
A comfortable living room showcases wooden beams on the ceiling and warm hardwood flooring. Two seating areas are present, one featuring a light sofa and the other a turquoise armchair. A decorative rug lies beneath, and a fireplace with plants adds a cozy touch.
Home in Catskill
4.94 out of 5 average rating, 109 reviews

Catskill Lumber House "Blue" - In Catskill Village

PaulRating, 5 stars4 months ago
truly wonderful and considerate hosts! absolutely a wonderful stay and will 100% be back next time we are in town!
Guest favorite
A private house is framed by a white picket fence, with a gravel driveway leading to an entrance. Surrounding greenery and colorful trees hint at a natural, serene environment. The structure features a mix of siding and a chimney, suggesting a cozy, country aesthetic.
Home in Craryville
4.92 out of 5 average rating, 113 reviews

The Gatehouse at Raspberry Ridge

JenniferRating, 5 stars3 days ago
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

Top guest favorite
An inviting kitchen and dining area features wood beams and large windows allowing natural light. A wooden table is surrounded by mid-century chairs. The kitchen is equipped with modern appliances and ample storage, creating a functional and open space for meals.
Home in Craryville
4.98 out of 5 average rating, 217 reviews

Modern Home in Woods w/ Hot Tub 10 Miles to Hudson

LeahRating, 5 stars3 days ago
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.
Top guest favorite
A modern house is surrounded by trees with colorful autumn leaves. The exterior features a wraparound deck, and snow lightly covers the ground and plants. Clear blue skies enhance the peaceful outdoor setting, creating a serene atmosphere.
Home in Rhinebeck
4.91 out of 5 average rating, 230 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

AudreyRating, 5 stars1 month ago
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!
Guest favorite
A private mid-century country home is seen nestled at the edge of a grassy clearing, surrounded by lush trees. The home features a simple design with a light-colored exterior, under a partly cloudy sky, creating a serene and tranquil setting.
Home in Hudson
4.95 out of 5 average rating, 151 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

SpencerRating, 5 stars3 weeks ago
Lovely place to stay. Close to Hudson, but far enough to feel secluded.
Guest favorite
A cozy living area features a light grey sofa with a decorative pillow. A bookshelf filled with a variety of books stands nearby, and a wooden chest adds character. Art pieces hang on the wall, while a glimpse of a hallway leading elsewhere is visible.
Home in Elizaville
4.86 out of 5 average rating, 101 reviews

Peaceful Hudson Valley Retreat House with HOT TUB!

JessicaRating, 5 stars2 weeks ago
Great spot to gather with friends. So close to trails and lovely towns. Loved the wood stove and hot tub!
Top guest favorite
The exterior of the farmhouse is captured, showcasing a charming white facade with a screened-in porch. Lush green trees surround the property, with a vibrant red tree providing a pop of color. A spacious grassy area is visible, leading to a wooden deck.
Home in Colebrook
4.99 out of 5 average rating, 221 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

JoshuaRating, 5 stars1 week ago
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!
Superhost
A red guest house is nestled among tall trees in a woodland setting. Large windows allow natural light to fill the interior, while the surrounding forest provides a serene backdrop. Leafy undergrowth and a carpet of dried leaves cover the ground in front of the house.
Home in Red Hook
4.88 out of 5 average rating, 230 reviews

Wooded Retreat w/ Hot Tub and Trout River

StephanieRating, 5 stars3 days ago
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.
Guest favorite
An aerial view showcases a serene lake bordered by lush greenery and trees, with the elegant cottage nestled among them. A private dock extends into the calm waters, reflecting the surrounding nature. The expansive landscape emphasizes the cottage's tranquil, waterfront location.
Home in Great Barrington
4.96 out of 5 average rating, 166 reviews

Elegant Year-Round Lakeside Retreat with AC

CristinaRating, 5 stars1 month ago
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!
Guest favorite
A hot tub sits on a polished wooden deck, surrounded by greenery. Soft lighting from string lights illuminates the area. A colorful striped pillow rests on a lounge chair, with a patterned plate and drink placed nearby, creating a relaxing outdoor retreat.
Home in Great Barrington
4.94 out of 5 average rating, 112 reviews

Best of the Berkshires + Hot Tub by Evergreen Home

StephenRating, 5 stars2 weeks ago
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

Guest favorite
A private heated pool area is surrounded by a spacious patio, featuring lounge chairs and a shaded table. The red two-story cabin is visible in the background, with large windows and step access to the pool area. Lush greenery completes the inviting outdoor space.
Home in Stanfordville
4.96 out of 5 average rating, 48 reviews

Charming lakeside cabin with private heated pool

JustinRating, 5 stars7 months ago
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!
Top guest favorite
A charming white farmhouse is framed by tall trees and lush greenery. The home features dark green shutters and a covered front entrance. Surrounding gardens with blooming flowers contribute to a serene outdoor setting, making the property inviting and spacious.
Home in Germantown
4.98 out of 5 average rating, 58 reviews

Columbia County Farmhouse with Pool

CarolineRating, 5 stars2 weeks ago
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!
Superhost
A central living space features a spiral staircase and high cathedral ceilings supported by wooden beams. Light streams through large windows, illuminating a mix of white sofas and chairs positioned on a natural fiber rug. The open layout connects to the kitchen area in the background.
Home in Stanfordville
5 out of 5 average rating, 5 reviews

The Round House w/ Heated Pool

JonathanRating, 5 stars5 months ago
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.
Guest favorite
A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.
Home in Ghent
4.88 out of 5 average rating, 313 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

michaelRating, 5 stars1 month ago
there was lots to do inside the house as well as outside. everything was amazing
Superhost
The exterior of the farmhouse is presented, featuring a white clapboard façade and a gabled roof. Several large windows allow natural light, while a stone staircase leads to the entrance. A shaded area is furnished with chairs, surrounded by green lawn and trees.
Home in Ghent
4.9 out of 5 average rating, 10 reviews

Farmhouse and Guesthouse w Pool, Pond and Sauna!

DavidRating, 5 stars20 months ago
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!
Guest favorite
Home in East Chatham
4.9 out of 5 average rating, 20 reviews

10 Acre Country Estate with Pool, Hot Tub & Views!

DeborahRating, 5 stars1 month ago
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
Guest favorite
Home in Sheffield
4.96 out of 5 average rating, 23 reviews

Peaceful and Private Setting

KellyRating, 5 stars2 months ago
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.
Guest favorite
A two-story house with a light exterior features a spacious front porch lined with railings. Symmetrical windows on the upper level complement the three dormer windows, while a chimney adds a classic touch. A well-maintained lawn surrounds the property.
Home in Clinton Corners
5 out of 5 average rating, 8 reviews

Family home in the country

CeciliaRating, 5 stars6 months ago
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

Destinations to explore