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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Home in Great Barrington
Berkshires Family Oasis with Hot Tub, Patio, Gym
4 bedrooms, 7 beds, 2.5 bathrooms
13–18 Sept
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4.98 out of 5 average rating, 50 reviews
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds
14–19 Sept
4.97 out of 5 average rating, 141 reviews
Top guest favourite
Home in Great Barrington
Sauna + Hot Tub Escape | Private & Pet Friendly
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 56 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds
20–25 Sept
4.92 out of 5 average rating, 193 reviews
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds
25–30 Oct
4.93 out of 5 average rating, 158 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
13–18 Sept
4.95 out of 5 average rating, 175 reviews
Top guest favourite
Home in Great Barrington
Fall Foliage @ The Barrington House: GB
5 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
3 bedrooms, 4 beds
1–6 Oct
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
2 bedrooms, 3 beds
18–23 Sept
5.0 out of 5 average rating, 149 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 83 reviews
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds
14–19 Sept
4.87 out of 5 average rating, 31 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds
13–18 Sept
4.9 out of 5 average rating, 10 reviews
Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
2 bedrooms, 3 beds
25–30 Oct
4.94 out of 5 average rating, 294 reviews
Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed
20–25 Sept
4.92 out of 5 average rating, 182 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed
1–6 Dec
4.93 out of 5 average rating, 353 reviews
Top guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires
1 king bed
20–25 Sept
4.94 out of 5 average rating, 189 reviews
Top guest favourite
Loft in Great Barrington
The Nest 5 min walk to downtown Great Barrington
1 bedroom, 1 queen bed
2–7 Oct
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Home in Great Barrington
Berkshire Bliss: Nature + Luxe
5 bedrooms, 7 beds
14–19 Oct
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Great Barrington
Never too early to book for the Holidays & NYE!
4 bedrooms, 5 beds
8–13 Oct
4.91 out of 5 average rating, 141 reviews