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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 bed, 1 private bathroom
13–18 Sept
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4.93 out of 5 average rating, 224 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed
13–18 Sept
4.9 out of 5 average rating, 80 reviews
Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds
13–18 Sept
4.94 out of 5 average rating, 88 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
Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 queen beds
26–31 Oct
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Home in Great Barrington
Modern Victorian- Walk to Town
4 bedrooms, 7 beds
14–19 Sept
4.97 out of 5 average rating, 142 reviews
Superhost
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
3 bedrooms, 4 beds
11–16 Sept
4.88 out of 5 average rating, 24 reviews
Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
2 bedrooms, 3 beds
20–25 Sept
4.94 out of 5 average rating, 294 reviews
Top guest favourite
Home in Great Barrington
Close to Butternut Ski with Views & Cozy Fireplace
3 bedrooms, 5 beds
12–17 Sept
5.0 out of 5 average rating, 39 reviews
Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds
11–16 Sept
Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed
28 Sept – 3 Oct
4.92 out of 5 average rating, 181 reviews
Top guest favourite
Home in Great Barrington
Walk to Town! Great Barrington 4-bedroom farmhouse
4 bedrooms, 4 beds
26–31 Oct
5.0 out of 5 average rating, 116 reviews
Guest favourite
Home in Great Barrington
Berkshires Family Oasis with Hot Tub, Patio, Gym
4 bedrooms, 7 beds
11–16 Sept
4.98 out of 5 average rating, 50 reviews
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 59 reviews
Guest favourite
Home in Great Barrington
Perfect Nature Retreat In Great Barrington
3 bedrooms, 3 beds
12–17 Sept
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Bungalow in Egremont
3-bedroom Berkshire bungalow on 2.5 peaceful acres
3 bedrooms, 5 beds
13–18 Sept
4.99 out of 5 average rating, 140 reviews
Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds
11–16 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds
16–21 Nov
4.98 out of 5 average rating, 49 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds
11–16 Sept
4.9 out of 5 average rating, 10 reviews