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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Home in Great Barrington
Walk to Town! Great Barrington 4-bedroom farmhouse
4 bedrooms, 4 beds, 2 private bathrooms
13–18 Oct
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5.0 out of 5 average rating, 111 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
4.89 out of 5 average rating, 62 reviews, 1 bed, 1 bathroom
19–24 Jul
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
4.95 out of 5 average rating, 168 reviews, 3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
4.91 out of 5 average rating, 167 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Cottage in Great Barrington
Artist Cottage
4.93 out of 5 average rating, 345 reviews, 1 bedroom, 1 bed, 2 bathrooms
2–7 Aug
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
4.94 out of 5 average rating, 181 reviews, 2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Home in Great Barrington
Private Home in The Berkshires (New Hot Tub!)
4.99 out of 5 average rating, 124 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Dec
Top guest favourite
Loft in Great Barrington
The Old Red Barn
4.99 out of 5 average rating, 364 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Sept
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
4.95 out of 5 average rating, 417 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Aug
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4.99 out of 5 average rating, 92 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
Top guest favourite
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 2 beds, 1 bathroom
25–30 Jul
Top guest favourite
Guest suite in Great Barrington
The Serendipity Spot
4.94 out of 5 average rating, 53 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Cabin in Great Barrington
Modern Luxury Log Cabin
4.96 out of 5 average rating, 114 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
Guest favourite
Cabin in Great Barrington
Kenyon's Cabin
4.91 out of 5 average rating, 32 reviews, 2 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
25–30 Aug
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4.95 out of 5 average rating, 183 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
13–18 Sept
Guest favourite
Home in Egremont
24 Main - The Egremont Village House
5.0 out of 5 average rating, 23 reviews, 7 bedrooms, 7 beds, 4.5 bathrooms
12–17 Aug
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
4.93 out of 5 average rating, 152 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
5.0 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 3 bathrooms
9–14 Aug