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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
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4.94 out of 5 average rating, 292 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
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds
9–14 Sept
4.97 out of 5 average rating, 140 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
8–13 Sept
4.95 out of 5 average rating, 175 reviews
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 queen beds
26–31 Oct
4.98 out of 5 average rating, 46 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
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds
10–15 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
6 bedrooms, 8 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 66 reviews
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds
9–14 Sept
4.87 out of 5 average rating, 31 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds
9–14 Sept
4.99 out of 5 average rating, 94 reviews
Guest favourite
Home in Great Barrington
Sunsets On Blue Hill, Newly Renovated Farmhouse
4 bedrooms, 6 beds
8–13 Sept
4.94 out of 5 average rating, 84 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 46 reviews
Guest favourite
Home in Great Barrington
Charming, view, large deck, private/walk downtown
3 bedrooms, 4 beds
9–14 Sept
4.89 out of 5 average rating, 101 reviews
Guest favourite
Home in Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4 bedrooms, 4 beds
8–13 Sept
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds
10–15 Sept
5.0 out of 5 average rating, 83 reviews
Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds
8–13 Sept
Guest favourite
Home in Great Barrington
Hilltop Ski and Sun Chalet with Hot Tub
5 bedrooms, 6 beds
13–18 Sept
4.97 out of 5 average rating, 61 reviews
Guest favourite
Home in Great Barrington
Renovated Downtown Great Barrington House
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.99 out of 5 average rating, 76 reviews