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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 bed, 2 private bathrooms
13–18 Sept
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4.93 out of 5 average rating, 347 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed, 1 bathroom
2–7 Aug
4.89 out of 5 average rating, 66 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
23–28 Sept
4.99 out of 5 average rating, 92 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 82 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill
4 bedrooms, 6 beds, 4 bathrooms
10–15 Sept
4.83 out of 5 average rating, 41 reviews
Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed, 1 bathroom
22–27 Aug
4.96 out of 5 average rating, 186 reviews
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
1 bedroom, 1 queen bed, 1 bathroom
21–26 Oct
4.95 out of 5 average rating, 421 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 185 reviews
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds, 3.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 57 reviews
Guest favourite
Home in Great Barrington
Never too early to book for the Holidays & NYE!
4 bedrooms, 5 beds, 2 bathrooms
3–8 Sept
4.91 out of 5 average rating, 139 reviews
Guest favourite
Cottage in Egremont
Kayak on Prospect Lake, Paddle Boards, Swim Dock+!
3 bedrooms, 5 beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 53 reviews
Superhost
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
3 bedrooms, 4 beds, 1.5 bathrooms
29 Aug – 3 Sept
4.86 out of 5 average rating, 22 reviews
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
27 Aug – 1 Sept
4.99 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, 154 reviews
Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.95 out of 5 average rating, 84 reviews
Home in Egremont
Nature Retreat Near Prospect Lake
3 bedrooms, 6 beds, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 queen beds, 2.5 bathrooms
13–18 Sept
4.95 out of 5 average rating, 185 reviews