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Search results; Over 1,000 homes in Great Barrington

Room in Great Barrington
Granville House - Queen traditional
1 bedroom, 1 bed, 1 shared bathroom
6–11 Sept
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5.0 out of 5 average rating, 31 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
4.89 out of 5 average rating, 64 reviews, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
4.88 out of 5 average rating, 8 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4.99 out of 5 average rating, 92 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
23–28 Sept
Home in Egremont
Nature Retreat Near Prospect Lake
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 6 beds, 1 bathroom
17–22 Aug
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
4.98 out of 5 average rating, 42 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Oct – 1 Nov
Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
4.96 out of 5 average rating, 185 reviews, 1 bed, 1 bathroom
22–27 Aug
Top guest favourite
Guest house in Great Barrington
Berkshires Guest Barn
4.97 out of 5 average rating, 33 reviews, 2 bedrooms, 5 beds, 1 bathroom
23–28 Aug
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
4.94 out of 5 average rating, 185 reviews, 2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
Top guest favourite
Cottage in Monterey
Beaver Lodge
5.0 out of 5 average rating, 82 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Sept
Guest favourite
Home in Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill
4.83 out of 5 average rating, 41 reviews, 4 bedrooms, 6 beds, 4 bathrooms
10–15 Sept
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4.95 out of 5 average rating, 184 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
13–18 Sept
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
4.96 out of 5 average rating, 25 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
Top guest favourite
Guest suite in Great Barrington
The Serendipity Spot
4.94 out of 5 average rating, 54 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
4.95 out of 5 average rating, 84 reviews, 3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
4.96 out of 5 average rating, 25 reviews, 3 bedrooms, 4 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Bungalow in Egremont
3-bedroom Berkshire bungalow on 2.5 peaceful acres
4.99 out of 5 average rating, 135 reviews, 3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
4.99 out of 5 average rating, 67 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Home in Great Barrington
Never too early to book for the Holidays & NYE!
4.91 out of 5 average rating, 138 reviews, 4 bedrooms, 5 beds, 2 bathrooms
3–8 Sept