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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Berkshires
Studio, 1 bed, 1 private bathroom
2–7 Sept
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4.87 out of 5 average rating, 135 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
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
14–19 Sept
4.95 out of 5 average rating, 173 reviews
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 59 reviews
Superhost
Home in Great Barrington
Woodland - Stunning 5 bedroom home in GB!
5 bedrooms, 10 beds
27 Sept – 2 Oct
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, 138 reviews
Home in Great Barrington
Garden Retreat, 1st fl KING ste, EV, close to all
3 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds
7–12 Sept
4.93 out of 5 average rating, 29 reviews
Guest favourite
Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
3 bedrooms, 4 beds
1–6 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Home in Great Barrington
River Cottage - Riverfront Home in Walkable Commun
3 bedrooms, 3 beds
3–8 Sept
4.95 out of 5 average rating, 65 reviews
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio
1 king bed
7–12 Sept
4.83 out of 5 average rating, 112 reviews
Superhost
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
3 bedrooms, 4 beds
7–12 Sept
4.86 out of 5 average rating, 22 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 Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds
6–11 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Great Barrington
Modern Victorian- Walk to Town
4 bedrooms, 7 beds
14–19 Sept
4.97 out of 5 average rating, 142 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed
30 Oct – 4 Nov
4.93 out of 5 average rating, 352 reviews
Top guest favourite
Home in Great Barrington
GB at your doorstep
3 bedrooms, 4 beds
9–14 Sept
4.94 out of 5 average rating, 139 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds
13–18 Sept
4.92 out of 5 average rating, 192 reviews
Guest favourite
Home in Great Barrington
Berkshires Retreat!
5 bedrooms, 9 beds
9–14 Sept
4.97 out of 5 average rating, 39 reviews