filters

Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 private bathrooms
8–13 Sept
,
5.0 out of 5 average rating, 43 reviews
Guest favourite
Flat in Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
1 king bed
7–12 Sept
4.89 out of 5 average rating, 178 reviews
Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed
6–11 Sept
4.96 out of 5 average rating, 191 reviews
Home in Great Barrington
Garden Retreat, 1st fl KING ste, EV, close to all
3 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 3 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
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
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
6–11 Sept
4.95 out of 5 average rating, 173 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds
13–18 Sept
4.94 out of 5 average rating, 191 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, 138 reviews
Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds
8–13 Sept
New place to stay
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, 16 reviews
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
1 bedroom, 1 queen bed
26–31 Oct
4.95 out of 5 average rating, 425 reviews
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds
7–12 Sept
4.93 out of 5 average rating, 29 reviews
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds
14–19 Sept
4.99 out of 5 average rating, 71 reviews
Guest favourite
Home in Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill
4 bedrooms, 6 beds
10–15 Sept
4.83 out of 5 average rating, 42 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
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds
6–11 Sept
4.91 out of 5 average rating, 173 reviews
Top guest favourite
Home in Great Barrington
Fall Foliage @ The Barrington House: GB
5 bedrooms, 6 beds
13–18 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds
9–14 Sept
4.97 out of 5 average rating, 138 reviews