
Holiday rentals in Great Barrington
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Top-rated holiday rentals in Great Barrington
Guests agree: these stays are highly rated for location, cleanliness and more.
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Top guest favourite

Home in Athens
5 out of 5 average rating, 38 reviewsPerfect home for a getaway from NYC
ScottRating, 5 stars3 weeks ago
Antonio and Yoon's place was perfect for our large group and dog. It's a very spacious home that is thoughtfully designed and in a lovely residential community. The beds and furniture were extremely comfortable, the backyard huge with a large patio and a fire pit. The six bedrooms, three full bathrooms, two living rooms, dining room, fully stocked kitchen, and finished basement gave our group of ten adults more than enough room to both gather together and enjoy time on our own. The location is near wonderful hikes and great restaurants and shops in Athens, Catskill, Hudson, and more. Antonio and Yoon were proactive, friendly, and clear in all communications. Highly recommended!
Top guest favourite

Home in Hillsdale
5 out of 5 average rating, 56 reviewsLakefront close to ski & shopping
KathyRating, 5 stars2 months ago
A beautiful home and the views were breathtaking on the lake. Although, it was frozen. All the amenities we needed and more. Close to skiing and tubing. Owner Sara was very attentive to respond quickly. We just wanted a getaway place for a family weekend. The road was narrow and very icy. Would go back but not in the winter. Summer and the Fall I think would be best. Lots more things to do in the nicer weather months. Thank you Sara for your hospitality.
Top guest favourite

Home in Millerton
4.97 out of 5 average rating, 181 reviewsVacation Home In Millerton
SarahRating, 5 stars1 week ago
We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!
Top guest favourite

Home in Charlemont
4.95 out of 5 average rating, 56 reviewsTall Pines Rental
GeorgiaRating, 5 stars2 weeks ago
It's hands down one of the best AirBnBs in the area! I've stayed at three different homes in the Charlemont area over the past three years, and this is by far the best. The home is in a perfect location near town, yet still feels private and secluded. It had everything we needed to make our stay seamless (keyless entry, TV, heat, all the kitchen utensils you could think of, extra amenities in the bathroom, etc.) They are also incredibly welcoming to pets - they even have extra dog bowls and a dog bed! If you're looking for a beautiful space that feels like home (with a reasonable price), this is it!
Guest favourite

Chalet in Athens
4.86 out of 5 average rating, 49 reviewsLarge & Sunny Lakefront Home-kayaks/fire pit/games
KatieRating, 5 stars4 days ago
This was such a relaxing home to spend a celebratory weekend in! We had a great time at Adnan's home over the weekend. The setting is so peaceful, right on the water and we enjoyed the fire pit one evening. The space is large, with plenty of room for all. The house is a little bit dated, but with that said, it had everything we needed for a lake-weekend! On top of that, Adnan could not have been more accommodating and responsive.
Top guest favourite

Home in Lanesborough
5 out of 5 average rating, 16 reviewsBerkshire Mountain House
DestinyRating, 5 stars1 week ago
This Airbnb exceeded our expectations! The house is spacious and super family friendly (also great for just adults). We loved the Airbnb so much that we only left the house once. Our hosts were very attentive and accommodating. I would recommend to anyone who is looking for a getaway in the Berkshires no matter the season.
Guest favourite

Home in Athens
4.91 out of 5 average rating, 11 reviewsCozy Catskill Getaway by Hudson
PaulaRating, 5 stars4 days ago
Lovely and cozy house, perfect for families! We will be back with nicer weather! Perfect house to make you feel at home with a lot of games to keep everybody entertained
Top guest favourite

Home in Averill Park
4.96 out of 5 average rating, 159 reviewsCozy, peaceful lake house close to Jiminy Peak
JenRating, 5 stars1 month ago
We loved our late winter stay on the lake - it was very peaceful and we had some great bird-watching opportunities. The art and special objects in the house made for a very cozy and beautiful environment. Overall, it was very comfortable and we would definitely stay again.
Quick stats about holiday rentals in Great Barrington
Total rentals
240 properties
Total number of reviews
10K reviews
Family-friendly rentals
160 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Destinations to explore
- Hudson Valley Holiday rentals
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- Rentals with a firepit Great Barrington
- Family-friendly rentals Great Barrington
- Rentals with a fireplace Great Barrington
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- Rentals with a patio Great Barrington
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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