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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds, 1.5 private bathrooms
6–11 Sept
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4.93 out of 5 average rating, 152 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed, 1 bathroom
19–24 Jul
4.89 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed, 1 bathroom
26–31 Jul
4.91 out of 5 average rating, 167 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
4.99 out of 5 average rating, 364 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
4.95 out of 5 average rating, 168 reviews
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.95 out of 5 average rating, 417 reviews
Top guest favourite
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
4 bedrooms, 2 queen beds, 1 bathroom
25–30 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill
4 bedrooms, 6 beds, 4 bathrooms
10–15 Sept
4.83 out of 5 average rating, 41 reviews
Guest favourite
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
3 bedrooms, 4 beds, 1.5 bathrooms
29 Aug – 3 Sept
4.9 out of 5 average rating, 21 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 343 reviews
Top guest favourite
Cabin in Great Barrington
Modern Luxury Log Cabin
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
4.96 out of 5 average rating, 114 reviews
Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 beds, 2 bathrooms
12–17 Oct
4.98 out of 5 average rating, 41 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 52 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
2–7 Aug
4.91 out of 5 average rating, 160 reviews
Top guest favourite
Home in Lee
Berkshire 4 season home
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 248 reviews
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds, 3.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 55 reviews
Guest favourite
Home in Great Barrington
In the middle of it all
3 bedrooms, 4 beds, 3.5 bathrooms
7–12 Aug
4.93 out of 5 average rating, 14 reviews
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 65 reviews
Guest favourite
Home in Egremont
24 Main - The Egremont Village House
7 bedrooms, 7 beds, 4.5 bathrooms
12–17 Aug
5.0 out of 5 average rating, 23 reviews