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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
7–12 Sept
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4.93 out of 5 average rating, 342 reviews
Top guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed
22–27 Aug
4.92 out of 5 average rating, 204 reviews
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, 164 reviews
Top guest favourite
Room in Great Barrington
Cozy & Convenient
1 queen bed
18–23 Jul
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Flat in Great Barrington
The River’s Whisper
2 bedrooms, 2 queen beds
16–21 Sept
4.98 out of 5 average rating, 40 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, 363 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds
28 Jul – 2 Aug
4.94 out of 5 average rating, 178 reviews
Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
3 bedrooms, 3 beds
11–16 Jul
New place to stay
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, 416 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
Top 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, 210 reviews
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds
2–7 Aug
4.98 out of 5 average rating, 65 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, 14 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, 113 reviews
Superhost
Home in Great Barrington
Prime Location, Recently Redesigned, Riverfront!
4 bedrooms, 6 beds
10–15 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds
2–7 Aug
4.91 out of 5 average rating, 159 reviews
Guest favourite
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
3 bedrooms, 4 beds
29 Aug – 3 Sept
4.9 out of 5 average rating, 21 reviews
Guest favourite
Home in Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill
4 bedrooms, 6 beds
10–15 Sept
4.83 out of 5 average rating, 41 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
12–17 Jul
4.95 out of 5 average rating, 167 reviews