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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 bed, 1 private bathroom
22–27 Aug
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4.94 out of 5 average rating, 214 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
9–14 Sept
4.99 out of 5 average rating, 92 reviews
Top guest favourite
Loft in Great Barrington
The Nest 5 min walk to downtown Great Barrington
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 61 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
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
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
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
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
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
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
Home in Great Barrington
Spacious and Rustic retreat in the Berkshires
4 bedrooms, 6 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Great Barrington
King Bed|Berkshires|2m Ski Resort|Patio|Wi-Fi
1 king bed, 1 bathroom
23–28 Aug
4.88 out of 5 average rating, 165 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
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
30 Aug – 4 Sept
4.93 out of 5 average rating, 348 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
Cottage by the Lake | Hiking, Skiing & Attractions
2 bedrooms, 4 beds, 1 bathroom
24–29 Aug
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
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
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