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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Home in Great Barrington
Berkshires Family Oasis with Hot Tub, Patio, Gym
4 bedrooms, 7 beds, 2.5 bathrooms
14–19 Sept
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4.98 out of 5 average rating, 50 reviews
Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 182 reviews
Home in Great Barrington
Luxurious Victorian, Walking Distance to Town
4 bedrooms, 4.5 bathrooms
16–21 Sept
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
Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
Guest favourite
Home in Great Barrington
Waterfront Modern Lake Mansfield Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
14–19 Sept
4.96 out of 5 average rating, 79 reviews
Superhost
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
3 bedrooms, 4 beds, 1.5 bathrooms
14–19 Sept
4.88 out of 5 average rating, 24 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
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, 47 reviews
Top guest favourite
Home in Egremont
The Catamount Ski Haus with Pool & Hot Tub
4 bedrooms, 4 king beds, 4 bathrooms
14–19 Sept
5.0 out of 5 average rating, 73 reviews
Top guest favourite
Bungalow in Egremont
3-bedroom Berkshire bungalow on 2.5 peaceful acres
3 bedrooms, 5 beds, 2 bathrooms
20–25 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, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Great Barrington
Higgins House
3 bedrooms, 3 queen beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
6 bedrooms, 9 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 67 reviews
Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 294 reviews
Top guest favourite
Home in Great Barrington
Walk to Town! Great Barrington 4-bedroom farmhouse
4 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 116 reviews
Guest favourite
Home in Great Barrington
Perfect Nature Retreat In Great Barrington
3 bedrooms, 3 beds, 3 bathrooms
20–25 Sept
4.98 out of 5 average rating, 43 reviews
Guest favourite
Cabin in Great Barrington
Kenyon's Cabin
2 bedrooms, 4 beds, 1 bathroom
14–19 Sept
4.87 out of 5 average rating, 38 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 46 reviews