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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Guest suite in Great Barrington
Hillside Haven
1 bedroom, 2 beds, 1 private bathroom
7–12 Sept
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4.99 out of 5 average rating, 136 reviews
Guest favourite
Flat in Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
1 king bed, 1 bathroom
7–12 Sept
4.89 out of 5 average rating, 178 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
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, 1 bathroom
14–19 Sept
4.95 out of 5 average rating, 173 reviews
Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 192 reviews
Top guest favourite
Room in Great Barrington
Cozy & Convenient
1 queen bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
6–11 Sept
4.91 out of 5 average rating, 174 reviews
Top guest favourite
Home in Great Barrington
Sauna + Hot Tub Escape | Private & Pet Friendly
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 47 reviews
Guest favourite
Home in West Stockbridge
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
6 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
4.88 out of 5 average rating, 25 reviews
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.93 out of 5 average rating, 29 reviews
Guest favourite
Home in Great Barrington
River Cottage - Riverfront Home in Walkable Commun
3 bedrooms, 3 beds, 2 bathrooms
3–8 Sept
4.95 out of 5 average rating, 65 reviews
Home in Great Barrington
Garden Retreat, 1st fl KING ste, EV, close to all
3 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Great Barrington
GB at your doorstep
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.94 out of 5 average rating, 139 reviews
Superhost
Home in Great Barrington
Woodland - Stunning 5 bedroom home in GB!
5 bedrooms, 10 beds, 3 bathrooms
27 Sept – 2 Oct
Guest favourite
Home in Great Barrington
Sunsets On Blue Hill, Newly Renovated Farmhouse
4 bedrooms, 6 beds, 3 bathrooms
7–12 Sept
4.94 out of 5 average rating, 82 reviews
Top guest favourite
Home in Great Barrington
Beautiful House in the Woods: Huge Yard, Hot Tub
4 bedrooms, 5 beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.91 out of 5 average rating, 23 reviews