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 Jul
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4.98 out of 5 average rating, 127 reviews
Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed, 1 bathroom
5–10 Jul
4.95 out of 5 average rating, 174 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Great Barrington
Private Home in The Berkshires (New Hot Tub!)
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Jul
4.99 out of 5 average rating, 124 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
4.98 out of 5 average rating, 131 reviews
Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 beds, 2 bathrooms
6–11 Sept
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
4.99 out of 5 average rating, 91 reviews
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
6–11 Jul
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Great Barrington
Walt's Townhouse - Berkshire living at its best
3 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 83 reviews
Guest favourite
Flat in Great Barrington
Kitchenette|King Bed|Couch
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
4.89 out of 5 average rating, 180 reviews
Top guest favourite
Bungalow in Egremont
3-bedroom Berkshire bungalow on 2.5 peaceful acres
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 132 reviews
Top guest favourite
Home in Great Barrington
Hilltop Ski and Sun Chalet with Hot Tub
5 bedrooms, 6 beds, 3.5 bathrooms
5–10 Jul
4.97 out of 5 average rating, 58 reviews
Top guest favourite
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 142 reviews
Top guest favourite
Home in Great Barrington
GB at your doorstep
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
4.95 out of 5 average rating, 128 reviews
Top guest favourite
Room in Great Barrington
Quiet refuge in Great Barrington
1 queen bed, 1 bathroom
5–10 Jul
4.94 out of 5 average rating, 224 reviews
Guest favourite
Home in Great Barrington
Berkshires: hiking, theatre, dance & pickleball!
4 bedrooms, 5 beds, 2 bathrooms
3–8 Sept
4.91 out of 5 average rating, 135 reviews
Guest favourite
Guest suite in Great Barrington
The Serendipity Spot
1 bedroom, 1 bed, 1 bathroom
19–24 Jul
4.94 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires
1 king bed, 1 bathroom
6–11 Jul
4.93 out of 5 average rating, 159 reviews