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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
,
4.93 out of 5 average rating, 349 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds
9–14 Sept
4.99 out of 5 average rating, 93 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds
23–28 Aug
4.89 out of 5 average rating, 9 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
16–21 Aug
4.95 out of 5 average rating, 171 reviews
Top guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 king bed
30 Aug – 4 Sept
4.92 out of 5 average rating, 161 reviews
Top guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed
30 Aug – 4 Sept
4.92 out of 5 average rating, 212 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
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds
25–30 Oct
4.87 out of 5 average rating, 256 reviews
Guest favourite
Cottage in Egremont
Kayak on Prospect Lake, Paddle Boards, Swim Dock+!
3 bedrooms, 5 beds
12–17 Sept
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
1 bedroom, 1 queen bed
26–31 Oct
4.95 out of 5 average rating, 421 reviews
Top guest favourite
Loft in Great Barrington
The Nest 5 min walk to downtown Great Barrington
1 bedroom, 1 queen bed
20–25 Oct
5.0 out of 5 average rating, 63 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
Guest house in Great Barrington
Berkshires Guest Barn
2 bedrooms, 5 beds
16–21 Aug
4.94 out of 5 average rating, 36 reviews
Top guest favourite
Home in Great Barrington
GB at your doorstep
3 bedrooms, 4 beds
31 Aug – 5 Sept
4.94 out of 5 average rating, 138 reviews
Guest favourite
Cabin in Great Barrington
Kenyon's Cabin
2 bedrooms, 4 beds
10–15 Aug
4.91 out of 5 average rating, 35 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
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
3 bedrooms, 4 beds
29 Aug – 3 Sept
4.86 out of 5 average rating, 22 reviews
Guest favourite
Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
3 bedrooms, 4 beds
30 Aug – 4 Sept
4.96 out of 5 average rating, 26 reviews