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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
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed
23–28 Aug
4.9 out of 5 average rating, 67 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed
10–15 Aug
4.99 out of 5 average rating, 365 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds
10–15 Sept
5.0 out of 5 average rating, 83 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds
23–28 Aug
4.88 out of 5 average rating, 8 reviews
Guest favourite
Cottage in Egremont
Kayak on Prospect Lake, Paddle Boards, Swim Dock+!
3 bedrooms, 5 beds
2–7 Aug
4.98 out of 5 average rating, 53 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds
27 Oct – 1 Nov
4.98 out of 5 average rating, 42 reviews
Home in Great Barrington
Cozy Riverside Retreat in the Berkshires
3 bedrooms, 4 beds
23–28 Aug
4.48 out of 5 average rating, 27 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds
20–25 Sept
4.94 out of 5 average rating, 186 reviews
Top guest favourite
Guest house in Great Barrington
Berkshires Guest Barn
2 bedrooms, 5 beds
16–21 Aug
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds
23–28 Sept
4.99 out of 5 average rating, 92 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds
7–12 Sept
4.98 out of 5 average rating, 54 reviews
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds
27 Aug – 1 Sept
4.99 out of 5 average rating, 67 reviews
Home in Egremont
Nature Retreat Near Prospect Lake
3 bedrooms, 6 beds
17–22 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed
25–30 Aug
4.93 out of 5 average rating, 347 reviews
Top guest favourite
Guest suite in Great Barrington
The Serendipity Spot
1 bedroom, 1 bed
2–7 Aug
4.94 out of 5 average rating, 54 reviews
Guest favourite
Guest house in Great Barrington
Trailside Cottage
1 bedroom, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed
22–27 Aug
4.96 out of 5 average rating, 186 reviews
Home in Great Barrington
Cottage by the Lake | Hiking, Skiing & Attractions
2 bedrooms, 4 beds
24–29 Aug