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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
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4.94 out of 5 average rating, 294 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 175 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
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Sept
4.87 out of 5 average rating, 31 reviews
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, 46 reviews
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.93 out of 5 average rating, 158 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 bathrooms
10–15 Sept
4.78 out of 5 average rating, 101 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 bathrooms
10–15 Sept
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds, 3.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Great Barrington
Modern Victorian- Walk to Town
4 bedrooms, 7 beds, 2.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 142 reviews
Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
6 bedrooms, 8 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 67 reviews
Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 88 reviews
Top guest favourite
Home in Great Barrington
Fall Foliage @ The Barrington House: GB
5 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 18 reviews
Superhost
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Sept
4.88 out of 5 average rating, 24 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
10–15 Sept
4.99 out of 5 average rating, 95 reviews
Guest favourite
Home in Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
4.92 out of 5 average rating, 24 reviews
Guest favourite
Home in Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill
4 bedrooms, 6 beds, 4 bathrooms
10–15 Sept
4.83 out of 5 average rating, 42 reviews
Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds, 2 bathrooms
10–15 Sept
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio
1 king bed, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 116 reviews