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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, 343 reviews
Top guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
4.92 out of 5 average rating, 205 reviews, 1 bed, 1 bathroom
22–27 Aug
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
4.95 out of 5 average rating, 167 reviews, 3 bedrooms, 4 beds, 1 bathroom
12–17 Jul
Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
4.96 out of 5 average rating, 179 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Loft in Great Barrington
The Old Red Barn
4.99 out of 5 average rating, 364 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Sept
Guest favourite
Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
4.96 out of 5 average rating, 23 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
Guest favourite
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
4.9 out of 5 average rating, 21 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
29 Aug – 3 Sept
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
4.96 out of 5 average rating, 23 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
New place to stay, 3 bedrooms, 3 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Home in Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4.89 out of 5 average rating, 18 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Great Barrington
Modern Victorian- Walk to Town
4.97 out of 5 average rating, 140 reviews, 4 bedrooms, 7 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Home in Great Barrington
In the middle of it all
4.93 out of 5 average rating, 14 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
7–12 Aug
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
4.98 out of 5 average rating, 65 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
4.91 out of 5 average rating, 159 reviews, 3 bedrooms, 4 beds, Toilet with sink
2–7 Aug
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4.96 out of 5 average rating, 181 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
8–13 Sept
Top guest favourite
Home in Great Barrington
Private Home in The Berkshires (New Hot Tub!)
4.99 out of 5 average rating, 124 reviews, 2 bedrooms, 2 beds, 1 bathroom
24–29 Aug
Top guest favourite
Home in Lee
Berkshire 4 season home
4.98 out of 5 average rating, 248 reviews, 3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
Top guest favourite
Home in Great Barrington
Seekonk Hill
4.98 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Sept