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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 bed, 1 private bathroom
8–13 Sept
,
4.99 out of 5 average rating, 368 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, 73 reviews
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, 189 reviews
Home in Great Barrington
Garden Retreat, 1st fl KING ste, EV, close to all
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 3 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, 46 reviews
Home in Great Barrington
Riverside in the Berkshires (with resident cat!)
3 bedrooms, 4 beds
23–28 Aug
4.53 out of 5 average rating, 32 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, 94 reviews
Guest favourite
Home in Great Barrington
2 Docks, Directly on Lake Buel, Sunsets: Sleeps 8!
4 bedrooms, 5 beds
20–25 Sept
4.94 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
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds
13–18 Sept
4.92 out of 5 average rating, 192 reviews
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds
14–19 Sept
4.99 out of 5 average rating, 69 reviews
Guest favourite
Home in Egremont
Nature Retreat Near Prospect Lake
3 bedrooms, 6 beds
7–12 Sept
5.0 out of 5 average rating, 7 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, 64 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, 424 reviews
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds
25–30 Oct
4.93 out of 5 average rating, 154 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
30 Aug – 4 Sept
4.95 out of 5 average rating, 173 reviews
Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 queen bed
22–27 Aug
4.94 out of 5 average rating, 218 reviews
Top guest favourite
Home in Great Barrington
GB at your doorstep
3 bedrooms, 4 beds
9–14 Sept
4.94 out of 5 average rating, 139 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 28 reviews