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Search results; Over 1,000 homes in Great Barrington

Guest house in Great Barrington
224 Lodge -Skiing/Entertainment
1 bedroom, 1 bed, 1 bathroom
16–21 Sept
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Top guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort
1 king bed
27 Sept – 2 Oct
4.87 out of 5 average rating, 251 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed
26 Sept – 1 Oct
4.99 out of 5 average rating, 370 reviews
Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 queen beds
26–31 Oct
4.98 out of 5 average rating, 48 reviews
Guest favourite
Home in Great Barrington
Berkshires Family Oasis with Hot Tub, Patio, Gym
4 bedrooms, 7 beds
15–20 Sept
4.98 out of 5 average rating, 50 reviews
Superhost
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
3 bedrooms, 4 beds
15–20 Sept
4.88 out of 5 average rating, 24 reviews
Top guest favourite
Guest house in Great Barrington
Trailside Cottage
1 bedroom, 3 beds
29 Oct – 3 Nov
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Great Barrington
Charming, view, large deck, private/walk downtown
3 bedrooms, 4 beds
21–26 Sept
4.89 out of 5 average rating, 102 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, 49 reviews
Top guest favourite
Guest suite in Great Barrington
Hillside Haven
1 bedroom, 2 beds
19–24 Sept
4.99 out of 5 average rating, 138 reviews
Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds
15–20 Sept
Guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed
4–9 Oct
4.92 out of 5 average rating, 221 reviews
Top guest favourite
Home in Great Barrington
Walt's Townhouse - Berkshire living at its best
3 bedrooms, 3 beds
29 Oct – 3 Nov
5.0 out of 5 average rating, 86 reviews
Guest favourite
Flat in Great Barrington
Beautfiul, modern, GB apartment
1 bedroom, 1 double bed
26–31 Oct
4.81 out of 5 average rating, 303 reviews
Top guest favourite
Home in Great Barrington
Fall Foliage @ The Barrington House: GB
5 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
2 bedrooms, 3 beds
25–30 Oct
4.94 out of 5 average rating, 294 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 176 reviews
Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds
15–20 Sept
5.0 out of 5 average rating, 49 reviews
Guest favourite
Home in Great Barrington
Waterfront Modern Lake Mansfield Retreat
3 bedrooms, 3 beds
16–21 Sept
4.96 out of 5 average rating, 79 reviews