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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Home in Great Barrington
Best of the Berkshires + Hot Tub by Evergreen Home
2 bedrooms, 2 beds, 1 private bathroom
8–13 Sept
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4.94 out of 5 average rating, 145 reviews
Guest favourite
Flat in Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
1 king bed, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 185 reviews
Guest favourite
Flat in Great Barrington
King Bed|Berkshires|2m Ski Resort|Patio|Wi-Fi
1 king bed, 1 bathroom
7–12 Sept
4.88 out of 5 average rating, 176 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
26 Sept – 1 Oct
4.99 out of 5 average rating, 370 reviews
Top guest favourite
Guest house in Great Barrington
Trailside Cottage
1 bedroom, 3 beds, 1 bathroom
29 Oct – 3 Nov
5.0 out of 5 average rating, 17 reviews
Home in Great Barrington
Luxurious Victorian, Walking Distance to Town
4 bedrooms, 4.5 bathrooms
7–12 Sept
Top guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 87 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
Superhost
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.87 out of 5 average rating, 23 reviews
Guest favourite
Home in Great Barrington
Charming, view, large deck, private/walk downtown
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.89 out of 5 average rating, 100 reviews
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
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 140 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
11–16 Sept
4.95 out of 5 average rating, 174 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
Fall Foliage @ The Barrington House: GB
5 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Great Barrington
Close to Butternut Ski with Views & Cozy Fireplace
3 bedrooms, 5 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 39 reviews
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, 192 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.9 out of 5 average rating, 10 reviews
Guest favourite
Home in Great Barrington
Perfect Nature Retreat In Great Barrington
3 bedrooms, 3 beds, 3 bathrooms
7–12 Sept
4.98 out of 5 average rating, 42 reviews