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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
2–7 Aug
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4.93 out of 5 average rating, 344 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed
19–24 Jul
4.89 out of 5 average rating, 62 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, 168 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed
1–6 Sept
4.99 out of 5 average rating, 364 reviews
Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed
26–31 Jul
4.91 out of 5 average rating, 167 reviews
Top guest favourite
Room in Great Barrington
Quiet refuge in Great Barrington
1 queen bed
6–11 Sept
4.93 out of 5 average rating, 229 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds
10–15 Aug
4.87 out of 5 average rating, 255 reviews
Top guest favourite
Cabin in Great Barrington
Modern Luxury Log Cabin
4 bedrooms, 6 beds
23–28 Aug
4.96 out of 5 average rating, 114 reviews
Top guest favourite
Home in Great Barrington
Private Home in The Berkshires (New Hot Tub!)
2 bedrooms, 2 queen beds
2–7 Dec
4.99 out of 5 average rating, 124 reviews
Top guest favourite
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
4 bedrooms, 2 queen beds
25–30 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
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
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds
2–7 Aug
4.99 out of 5 average rating, 92 reviews
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
1 bedroom, 1 queen bed
21–26 Oct
4.95 out of 5 average rating, 417 reviews
Guest favourite
Home in Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4 bedrooms, 4 beds
23–28 Aug
4.89 out of 5 average rating, 18 reviews
Guest favourite
Cabin in Great Barrington
Kenyon's Cabin
2 bedrooms, 4 beds
19–24 Jul
4.91 out of 5 average rating, 32 reviews
Top guest favourite
Guest suite in Great Barrington
The Serendipity Spot
1 bedroom, 1 bed
19–24 Jul
4.94 out of 5 average rating, 53 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds
27 Jul – 1 Aug
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Home in Lee
Berkshire 4 season home
3 bedrooms, 3 queen beds
25–30 Oct
4.98 out of 5 average rating, 248 reviews
Guest favourite
Home in Great Barrington
In the middle of it all
3 bedrooms, 4 beds
7–12 Aug
4.93 out of 5 average rating, 15 reviews