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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, 349 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, 43 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, 93 reviews
Top guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 212 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.89 out of 5 average rating, 9 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 Nest 5 min walk to downtown Great Barrington
1 bedroom, 1 queen bed, 1 bathroom
31 Aug – 5 Sept
5.0 out of 5 average rating, 62 reviews
Guest favourite
Flat in Great Barrington
King Bed|2mi Ski Resort|Fast Wi-Fi|Studio|
1 king bed, 1 bathroom
9–14 Aug
4.85 out of 5 average rating, 107 reviews
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.95 out of 5 average rating, 421 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.87 out of 5 average rating, 256 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
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
Cottage in Egremont
Kayak on Prospect Lake, Paddle Boards, Swim Dock+!
3 bedrooms, 5 beds, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 54 reviews
Guest favourite
Home in Great Barrington
Light & bright modern tree house
3 bedrooms, 3 beds, 3.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Great Barrington
The River’s Whisper
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Sept
4.98 out of 5 average rating, 47 reviews
Guest favourite
Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
3 bedrooms, 4 beds, 3 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 26 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
Guest favourite
Cabin in Great Barrington
Kenyon's Cabin
2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 35 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 54 reviews