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Search results; Over 1,000 homes in Great Barrington

Guest favorite
Home in Great Barrington
Waterfront retreat with a pickleball court
3 bedrooms, 3 beds, 2.5 private baths
Sep 14 – 19
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4.97 out of 5 average rating, 76 reviews
Guest favorite
Apartment in Great Barrington
Mid-century modern, walkable to restaurants
4.92 out of 5 average rating, 213 reviews, 1 bed, 1 bath
Aug 30 – Sep 4
Top guest favorite
Apartment in Great Barrington
Fire pit and a stroll to downtown
4.98 out of 5 average rating, 47 reviews, 2 bedrooms, 2 beds, 1 bath
Oct 13 – 18
Guest favorite
Home in Great Barrington
Front porch and fenced backyard in Housatonic
4.89 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 23 – 28
Guest favorite
Home in Great Barrington
Mountain views, hot tub, and a fire pit
4.91 out of 5 average rating, 22 reviews, 4 bedrooms, 4 beds, 2 baths
Aug 23 – 28
Guest favorite
Apartment in Great Barrington
Mid-century motel, 2 miles from skiing
4.88 out of 5 average rating, 132 reviews, 1 bed, 1 bath
Aug 23 – 28
Top guest favorite
Guest suite in Great Barrington
Modern hillside suite with a fire pit
4.99 out of 5 average rating, 135 reviews, 1 bedroom, 2 beds, 1 bath
Sep 7 – 12
Guest favorite
Cabin in Great Barrington
Fireplace and a private backyard
4.89 out of 5 average rating, 36 reviews, 2 bedrooms, 4 beds, 1 bath
Aug 23 – 28
Home in Great Barrington
Historic home right on the Housatonic
4.46 out of 5 average rating, 28 reviews, 3 bedrooms, 4 beds, 1 bath
Aug 23 – 28
Top guest favorite
Room in Great Barrington
Riverside farmhouse, walk to town
5.0 out of 5 average rating, 51 reviews, 1 queen bed, 1 bath
Aug 30 – Sep 4
Top guest favorite
Home in Great Barrington
1887 Victorian with garden and sauna
5.0 out of 5 average rating, 57 reviews, 3 bedrooms, 4 beds, 3.5 baths
Aug 25 – 30
Guest favorite
Guesthouse in Great Barrington
Renovated Victorian duplex in Housatonic
4.95 out of 5 average rating, 172 reviews, 3 bedrooms, 4 beds, 1 bath
Aug 16 – 21
Top guest favorite
Cottage in Great Barrington
Converted carriage house with a fire pit
4.93 out of 5 average rating, 154 reviews, 2 bedrooms, 3 beds, 1.5 baths
Oct 25 – 30
Top guest favorite
Cottage in Great Barrington
Artsy vintage cottage with a private lodge
4.93 out of 5 average rating, 350 reviews, 1 bedroom, 1 bed, 2 baths
Sep 21 – 26
Guest favorite
Guesthouse in Great Barrington
Renovated post-and-beam barn near skiing
4.95 out of 5 average rating, 37 reviews, 2 bedrooms, 5 beds, 1 bath
Aug 16 – 21
Top guest favorite
Home in Stockbridge
Renovated 1800s farmhouse on 5 acres
4.95 out of 5 average rating, 185 reviews, 2 bedrooms, 2 beds, 2.5 baths
Oct 18 – 23
Top guest favorite
Home in Great Barrington
Hot tub and sauna with mountain views
5.0 out of 5 average rating, 56 reviews, 3 bedrooms, 4 beds, 2 baths
Sep 27 – Oct 2
Top guest favorite
Guesthouse in Great Barrington
Trail and lake access near downtown
5.0 out of 5 average rating, 13 reviews, 1 bedroom, 3 beds, 1 bath
Sep 28 – Oct 3
Guest favorite
Home in Great Barrington
4 minutes to skiing with a fire pit
4.96 out of 5 average rating, 27 reviews, 3 bedrooms, 4 beds, 3 baths
Aug 30 – Sep 4