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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 bed, 1 private bathroom
8–13 Sept
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4.99 out of 5 average rating, 368 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed
23–28 Aug
4.91 out of 5 average rating, 74 reviews
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort
1 king bed
30 Aug – 4 Sept
4.87 out of 5 average rating, 241 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed
30 Oct – 4 Nov
4.93 out of 5 average rating, 351 reviews
Home in Great Barrington
Garden Retreat, 1st fl KING ste, EV, close to all
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Great Barrington
The River’s Whisper
2 bedrooms, 2 queen beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds
27 Oct – 1 Nov
4.98 out of 5 average rating, 46 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds
13–18 Sept
4.92 out of 5 average rating, 192 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds
9–14 Sept
4.99 out of 5 average rating, 94 reviews
Guest favourite
Cottage in Egremont
Kayak on Prospect Lake, Paddle Boards, Swim Dock+!
3 bedrooms, 5 beds
12–17 Sept
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds
10–15 Sept
5.0 out of 5 average rating, 83 reviews
Top guest favourite
Home in Great Barrington
GB at your doorstep
3 bedrooms, 4 beds
9–14 Sept
4.94 out of 5 average rating, 139 reviews
Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 queen bed
22–27 Aug
4.94 out of 5 average rating, 220 reviews
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds
25–30 Oct
4.93 out of 5 average rating, 154 reviews
Top guest favourite
Loft in Great Barrington
The Nest 5 min walk to downtown Great Barrington
1 bedroom, 1 queen bed
20–25 Oct
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 beds
26–31 Oct
4.98 out of 5 average rating, 45 reviews
Guest favourite
Home in Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4 bedrooms, 4 beds
23–28 Aug
4.91 out of 5 average rating, 23 reviews
Top guest favourite
Guest house in Great Barrington
Trailside Cottage
1 bedroom, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Egremont
Nature Retreat Near Prospect Lake
3 bedrooms, 6 beds
7–12 Sept
5.0 out of 5 average rating, 7 reviews