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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
19–24 Sept
,
4.99 out of 5 average rating, 137 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 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
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds
10–15 Sept
5.0 out of 5 average rating, 83 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, 157 reviews
Top guest favourite
Guest house in Great Barrington
Trailside Cottage
1 bedroom, 3 beds
29 Oct – 3 Nov
5.0 out of 5 average rating, 17 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, 352 reviews
Home in Great Barrington
Riverside Retreat in the Berkshires
3 bedrooms, 4 beds
20–25 Sept
4.57 out of 5 average rating, 35 reviews
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds
7–12 Sept
4.87 out of 5 average rating, 31 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
11–16 Sept
4.95 out of 5 average rating, 174 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
Guest favourite
Home in Great Barrington
River Cottage - Riverfront Home in Walkable Commun
3 bedrooms, 3 beds
7–12 Sept
4.96 out of 5 average rating, 67 reviews
Top guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds
13–18 Sept
4.94 out of 5 average rating, 88 reviews
Top guest favourite
Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
3 bedrooms, 4 beds
7–12 Sept
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Loft in Great Barrington
The Nest 5 min walk to downtown Great Barrington
1 bedroom, 1 queen bed
20–25 Oct
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
2 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 148 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
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, 140 reviews
Superhost
Room in Great Barrington
Quiet refuge in Great Barrington
1 queen bed
4–9 Oct
4.92 out of 5 average rating, 242 reviews