filters

Search results; Over 1,000 homes in Great Barrington

Photo 1 of 27
Guest favourite
Home in Great Barrington
Waterfront Modern Lake Mansfield Retreat
3 bedrooms, 3 beds, 2.5 private bathrooms
2–7 Nov
,
4.96 out of 5 average rating, 80 reviews
Photo 1 of 11
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
10–15 Nov
4.97 out of 5 average rating, 141 reviews
Photo 1 of 29
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
19–24 Oct
4.99 out of 5 average rating, 95 reviews
Photo 1 of 29
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 83 reviews
Photo 1 of 21
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
Photo 1 of 29
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 195 reviews
Photo 1 of 29
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 176 reviews
Photo 1 of 21
Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 21
Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 queen beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 48 reviews
Photo 1 of 14
Guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 king bed, 1 bathroom
20–25 Sept
4.91 out of 5 average rating, 176 reviews
Photo 1 of 29
Top guest favourite
Home in Great Barrington
Walt's Townhouse - Berkshire living at its best
3 bedrooms, 3 beds, 2 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 86 reviews
Photo 1 of 29
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds, 3.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 59 reviews
Photo 1 of 29
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
5–10 Nov
4.94 out of 5 average rating, 354 reviews
Photo 1 of 29
Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds, 3.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 50 reviews
Photo 1 of 29
Top guest favourite
Home in Great Barrington
RENOVATED BERKSHIRE COUNTRY CASTLE
3 bedrooms, 3 beds, 3 bathrooms
25–30 Sept
4.97 out of 5 average rating, 58 reviews
Photo 1 of 15
Top guest favourite
Cottage in Great Barrington
Cottage on Scenic Road
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.91 out of 5 average rating, 281 reviews
Photo 1 of 29
Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
6 bedrooms, 9 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 68 reviews
Photo 1 of 29
Guest favourite
Home in Great Barrington
Hilltop Ski and Sun Chalet with Hot Tub
5 bedrooms, 6 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 63 reviews
Photo 1 of 23
Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 88 reviews