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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Home in Great Barrington
Stylish colonial, 4 acres, 9 min Gt Barrington
4 bedrooms, 6 beds, 2 shared bathrooms
9–14 Sept
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4.91 out of 5 average rating, 101 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, 172 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, 213 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, 164 reviews
Flat in Egremont
Walk in the Park
2 bedrooms, 3 beds
13–18 Aug
Top guest favourite
Flat in Great Barrington
The River’s Whisper
2 bedrooms, 2 queen beds
13–18 Oct
4.98 out of 5 average rating, 47 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
Guest favourite
Home in Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4 bedrooms, 4 beds
23–28 Aug
4.91 out of 5 average rating, 22 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed
8–13 Sept
4.99 out of 5 average rating, 366 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, 423 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
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds
19–24 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Guest house in Great Barrington
Berkshires Guest Barn
2 bedrooms, 5 beds
16–21 Aug
4.95 out of 5 average rating, 37 reviews
Home in Great Barrington
Cottage by the Lake | Hiking, Skiing & Attractions
2 bedrooms, 4 beds
24–29 Aug
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds
27 Aug – 1 Sept
4.99 out of 5 average rating, 69 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
Top guest favourite
Guest suite in Great Barrington
Hillside Haven
1 bedroom, 2 beds
7–12 Sept
4.99 out of 5 average rating, 135 reviews
Top guest favourite
Home in Great Barrington
Sauna + Hot Tub Escape | Private & Pet Friendly
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 56 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