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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
4.92 out of 5 average rating, 203 reviews, 1 bed, 1 bathroom
22–27 Aug
Top guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
4.96 out of 5 average rating, 178 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Flat in Great Barrington
The River’s Whisper
4.97 out of 5 average rating, 39 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Sept
Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
New place to stay, 3 bedrooms, 3 beds, 2.5 bathrooms
11–16 Jul
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4.99 out of 5 average rating, 92 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
Top guest favourite
Loft in Great Barrington
The Old Red Barn
4.99 out of 5 average rating, 362 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 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
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Home in Great Barrington
Cozy Riverside Retreat in the Berkshires
4.5 out of 5 average rating, 24 reviews, 3 bedrooms, 4 beds, 1 bathroom
22–27 Aug
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
4.95 out of 5 average rating, 416 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Oct
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
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 Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4.88 out of 5 average rating, 17 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Great Barrington
Seekonk Hill
4.98 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 2 bathrooms
6–11 Sept
Superhost
Home in Great Barrington
Prime Location, Recently Redesigned, Riverfront!
5.0 out of 5 average rating, 6 reviews, 4 bedrooms, 6 beds, 2 bathrooms
10–15 Jul
Guest favourite
Home in Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill
4.83 out of 5 average rating, 41 reviews, 4 bedrooms, 6 beds, 4 bathrooms
10–15 Sept
Top guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
4.94 out of 5 average rating, 210 reviews, 1 bedroom, 1 bed, 1 bathroom
22–27 Aug
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