filters

Search results; Over 1,000 homes in Great Barrington

Photo 1 of 21
Top guest favourite
Home in Great Barrington
Sauna + Hot Tub Escape | Private & Pet Friendly
3 bedrooms, 4 beds, 2 private bathrooms
27 Sept – 2 Oct
,
5.0 out of 5 average rating, 56 reviews
Photo 1 of 29
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 176 reviews
Photo 1 of 29
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 83 reviews
Photo 1 of 29
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.93 out of 5 average rating, 160 reviews
Photo 1 of 11
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
10–15 Nov
4.97 out of 5 average rating, 141 reviews
Photo 1 of 29
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Oct
4.92 out of 5 average rating, 195 reviews
Photo 1 of 29
Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
6 bedrooms, 9 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 68 reviews
Photo 1 of 29
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 47 reviews
Photo 1 of 21
Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Guest favourite
Home in Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 25 reviews
Photo 1 of 29
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 bathrooms
28 Sept – 3 Oct
4.78 out of 5 average rating, 101 reviews
Photo 1 of 22
Hotel room in Lee
Endless Family Fun: Pools, Arcade Room & Mini Golf
2 bedrooms, 2 bathrooms
22–27 Sept
4.66 out of 5 average rating, 35 reviews
Photo 1 of 10
Superhost
Home in Great Barrington
Relaxing Housatonic Retreat
3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
4.7 out of 5 average rating, 128 reviews
Photo 1 of 29
Superhost
Home in Great Barrington
Prime Location, Recently Redesigned, Riverfront!
4 bedrooms, 6 beds, 2 bathrooms
27 Sept – 2 Oct
4.9 out of 5 average rating, 10 reviews
Photo 1 of 29
Guest favourite
Home in West Stockbridge
Spacious Retreat near Tanglewood & Ski Resorts
6 bedrooms, 7 beds, 3.5 bathrooms
8–13 Nov
4.88 out of 5 average rating, 25 reviews
Photo 1 of 27
Top guest favourite
Home in Lee
Berkshire 4 season home
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
4.98 out of 5 average rating, 252 reviews
Photo 1 of 29
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
4.87 out of 5 average rating, 31 reviews
Photo 1 of 29
Top guest favourite
Home in Great Barrington
RENOVATED BERKSHIRE COUNTRY CASTLE
3 bedrooms, 3 beds, 3 bathrooms
25–30 Sept
4.97 out of 5 average rating, 58 reviews
Photo 1 of 29
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 59 reviews