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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
Berkshires Black Abbey
5.0 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 3 bathrooms
9–14 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, 310 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
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
Top guest favourite
Cabin in Great Barrington
Modern Luxury Log Cabin
4.96 out of 5 average rating, 113 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Berkshires
4.89 out of 5 average rating, 123 reviews, 1 bed, 1 bathroom
5–10 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
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
Top guest favourite
Room in Great Barrington
Cozy & Convenient
5.0 out of 5 average rating, 45 reviews, 1 queen bed, 1 bathroom
7–12 Jul
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
Barn in New Marlborough
Hartsville Barn in the Berkshires
4.98 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
Top guest favourite
Home in Great Barrington
Berkshires Retreat!
5.0 out of 5 average rating, 36 reviews, 5 bedrooms, 9 beds, 2.5 bathrooms
9–14 Sept
Guest favourite
Home in Great Barrington
Berkshires Family Inn – For Getaways & Big Groups!
4.89 out of 5 average rating, 35 reviews, 7 bedrooms, 10 beds, 6.5 bathrooms
16–21 Aug
Guest favourite
Home in Great Barrington
Sunsets On Blue Hill, Newly Renovated Farmhouse
4.94 out of 5 average rating, 79 reviews, 4 bedrooms, 6 beds, 3 bathrooms
6–11 Jul
Guest favourite
Cabin in Great Barrington
Kenyon's Cabin
4.9 out of 5 average rating, 30 reviews, 2 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Great Barrington
Berkshire Vacation Home
4.98 out of 5 average rating, 54 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Great Barrington
Walk to Town! Great Barrington 4-bedroom farmhouse
5.0 out of 5 average rating, 111 reviews, 4 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
Home in Great Barrington
Charming, view, large deck, private/walk downtown
4.89 out of 5 average rating, 93 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Aug