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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
2 bedrooms, 3 beds, 2 private bathrooms
8–13 Sept
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5.0 out of 5 average rating, 145 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
28 Sept – 3 Oct
4.99 out of 5 average rating, 92 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 69 reviews
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Berkshires
1 king bed, 1 bathroom
23–28 Aug
4.88 out of 5 average rating, 130 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, 83 reviews
Home in Great Barrington
Cozy Riverside Retreat in the Berkshires
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
4.48 out of 5 average rating, 27 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.99 out of 5 average rating, 365 reviews
Top guest favourite
Home in Great Barrington
Berkshire Vacation Home
3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.98 out of 5 average rating, 54 reviews
Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
4.94 out of 5 average rating, 214 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
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, 187 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
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
Flat in Great Barrington
Beautfiul, modern, GB apartment
1 bedroom, 1 double bed, 1 bathroom
12–17 Oct
4.81 out of 5 average rating, 302 reviews
Guest favourite
Home in Egremont
24 Main - The Egremont Village House
7 bedrooms, 7 beds, 4.5 bathrooms
12–17 Aug
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Cabin in Great Barrington
Modern Luxury Log Cabin
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
4.97 out of 5 average rating, 115 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 171 reviews
Home in Great Barrington
Cottage by the Lake | Hiking, Skiing & Attractions
2 bedrooms, 4 beds, 1 bathroom
24–29 Aug