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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
Home in Great Barrington
Prime location for the best of the Berkshires
4.97 out of 5 average rating, 133 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Sept
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
4.96 out of 5 average rating, 165 reviews, 3 bedrooms, 4 beds, 1 bathroom
12–17 Jul
Top guest favourite
Cabin in Great Barrington
Modern Luxury Log Cabin
4.96 out of 5 average rating, 112 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
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
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 308 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
Guest favourite
Home in Great Barrington
Berkshires Retreat!
5.0 out of 5 average rating, 35 reviews, 5 bedrooms, 9 beds, 2.5 bathrooms
9–14 Sept
Guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
4.91 out of 5 average rating, 145 reviews, 1 bed, 1 bathroom
8–13 Jul
Top guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires
4.93 out of 5 average rating, 161 reviews, 1 bed, 1 bathroom
6–11 Jul
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
25–30 Aug
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
4.93 out of 5 average rating, 147 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
4.98 out of 5 average rating, 61 reviews, 6 bedrooms, 8 beds, 3 bathrooms
4–9 Jul
Guest favourite
Home in Great Barrington
Cozy Great Barrington Cottage with Mountain View
4.94 out of 5 average rating, 85 reviews, 4 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Top guest favourite
Home in Great Barrington
Seekonk Hill
4.97 out of 5 average rating, 39 reviews, 2 bedrooms, 2 beds, 2 bathrooms
6–11 Sept
Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
New place to stay, 3 bedrooms, 3 beds, 2.5 bathrooms
28 Jul – 2 Aug
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
4.9 out of 5 average rating, 157 reviews, 3 bedrooms, 4 beds, Toilet with sink
12–17 Jul
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
4.97 out of 5 average rating, 32 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Jul
Top guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
4.94 out of 5 average rating, 209 reviews, 1 bedroom, 1 bed, 1 bathroom
22–27 Aug
Top guest favourite
Home in Great Barrington
Walk to Town! Great Barrington 4-bedroom farmhouse
5.0 out of 5 average rating, 110 reviews, 4 bedrooms, 4 beds, 2 bathrooms
13–18 Oct