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Search results; Over 1,000 homes in West Stockbridge

Chalet in West Stockbridge
Modern Mtn Chalet | Great Barrington & Tanglewood
3 bedrooms, 10 beds, 2.5 private bathrooms
31 Aug – 5 Sept
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4.96 out of 5 average rating, 45 reviews
Top guest favourite
Guest house in West Stockbridge
Guest House 15 mins to Tanglewood
2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 28 reviews
Guest favourite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.95 out of 5 average rating, 150 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in West Stockbridge
Berkshires Forest Retreat with Hot Tub
3 bedrooms, 3 beds, 2 bathrooms
4–9 Sept
4.99 out of 5 average rating, 82 reviews
Top guest favourite
Home in West Stockbridge
Berkshires-Enjoy The Peak, private home
3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept
4.94 out of 5 average rating, 104 reviews
Guest favourite
Guest house in Canaan
Airy cottage with meadow views in The Berkshires
1 bedroom, 3 beds, 1 bathroom
8–13 Sept
4.93 out of 5 average rating, 207 reviews
Top guest favourite
Room in West Stockbridge
Standard Suite with a Patio at Shaker Mill Inn
3 beds, 1 bathroom
23–28 Jul
5.0 out of 5 average rating, 11 reviews
Home in Stockbridge
Light Filled - Modern Rustic Home
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Room in West Stockbridge
Standard Suite at Shaker Mill Inn
2 queen beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 queen beds, 2.5 bathrooms
31 Aug – 5 Sept
4.96 out of 5 average rating, 180 reviews
Top guest favourite
Home in Canaan
Crossings Cottage
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 90 reviews
Home in Stockbridge
Light-filled Carpenter's Cottage
1 bedroom, 1 bed, 1 bathroom
11–16 Jul
New place to stay
Guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 king bed, 1 bathroom
19–24 Jul
4.91 out of 5 average rating, 147 reviews
Top guest favourite
Room in Great Barrington
Quiet refuge in Great Barrington
1 queen bed, 1 bathroom
6–11 Sept
4.93 out of 5 average rating, 228 reviews
Guest favourite
Guest house in Stockbridge
Modern barn in the heart of the Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 157 reviews
Superhost
Room in West Stockbridge
Deluxe Suite with a Balcony Pets allowed
1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.95 out of 5 average rating, 43 reviews
Guest favourite
Home in West Stockbridge
West Stockbridge MA gem, in town and facing lake
2 bedrooms, 2 queen beds, 2 bathrooms
23–29 Jul
4.95 out of 5 average rating, 40 reviews