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Search results; Over 1,000 homes in Great Barrington

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
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5.0 out of 5 average rating, 56 reviews
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Sept
4.97 out of 5 average rating, 141 reviews
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
Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds, 3.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 49 reviews
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
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Sept
4.87 out of 5 average rating, 31 reviews
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds, 3.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Home in Great Barrington
Fall Foliage @ The Barrington House: GB
5 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 18 reviews
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
Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.94 out of 5 average rating, 88 reviews
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
Guest favourite
Home in West Stockbridge
Beautiful And Private Home Centrally Located
4 bedrooms, 7 beds, 3.5 bathrooms
21–26 Sept
4.96 out of 5 average rating, 67 reviews
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, 158 reviews
Top guest favourite
Home in Great Barrington
Cozy Great Barrington Cottage with Mountain View
4 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
4.95 out of 5 average rating, 91 reviews
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
Top guest favourite
Home in Great Barrington
Higgins House
3 bedrooms, 3 queen beds, 2.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Great Barrington
Woodland - Stunning 5 bedroom home in GB!
5 bedrooms, 10 beds, 3 bathrooms
27 Sept – 2 Oct
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