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Search results; Over 1,000 homes in West Stockbridge

Guest favourite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
3 bedrooms, 4 beds, 2 private bathrooms
7–12 Sept
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4.95 out of 5 average rating, 154 reviews
Guest favourite
Home in West Stockbridge
Modern Log Cabin w/Pool & Views By Evergreen Home
4 bedrooms, 5 beds, 3.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in West Stockbridge
Pixley Forest | 15 Mins To Tanglewood • Fireplace
4 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Guest house in West Stockbridge
Guest House 15 mins to Tanglewood
2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in West Stockbridge
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
6 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
4.88 out of 5 average rating, 25 reviews
Top guest favourite
Home in West Stockbridge
Secluded Chic Mountain Chalet near Tanglewood
3 bedrooms, 3 beds, 2 bathrooms
3–8 Sept
4.93 out of 5 average rating, 57 reviews
Guest favourite
Room in West Stockbridge
Standard Suite with a Patio at Shaker Mill Inn
3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cabin in West Stockbridge
Cozy, two-bedroom cabin in a wooded glen
2 bedrooms, 2 queen beds, 1 bathroom
31 Oct – 5 Nov
4.98 out of 5 average rating, 140 reviews
Top guest favourite
Home in West Stockbridge
Berkshires-Enjoy The Peak, private home
3 bedrooms, 3 beds, 2.5 bathrooms
30 Oct – 4 Nov
4.94 out of 5 average rating, 107 reviews
Guest favourite
Home in West Stockbridge
Farmhouse with Pool on 63 Acres
5 bedrooms, 5 beds, 3.5 bathrooms
1–8 Sept
4.94 out of 5 average rating, 17 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 172 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
30 Oct – 4 Nov
4.93 out of 5 average rating, 350 reviews
Top guest favourite
Cabin in Chatham
Rustic Secluded Cabin near Berkshires. *wood stove
4 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
4.92 out of 5 average rating, 143 reviews
Top guest favourite
Home in West Stockbridge
Berkshires Forest Retreat with Hot Tub
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
4.98 out of 5 average rating, 85 reviews
Superhost
Room in West Stockbridge
Family Suite with a Balcony at Shaker Mill Inn
2 beds, 1 bathroom
6–11 Sept
Top guest favourite
Barn in Town of Hillsdale
Blue Door Barn - Pond and Sweeping Views
1 bedroom, 2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 56 reviews
Guest favourite
Room in West Stockbridge
Standard Suite at Shaker Mill Inn
2 queen beds, 1 bathroom
31 Aug – 5 Sept
5.0 out of 5 average rating, 7 reviews