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Search results; Over 1,000 homes in West Stockbridge

Home in Massachusetts
1850's Berkshire farmhouse
5 bedrooms, 6 beds, 2 private bathrooms
19–24 Jul
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4.87 out of 5 average rating, 93 reviews
Guest house in Massachusetts
Guest House 15 mins to Tanglewood
2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 25 reviews
Home in Massachusetts
Pixley Forest | 15 Mins To Tanglewood • Fireplace
4 bedrooms, 6 beds, 2 bathrooms
16–21 Jul
5.0 out of 5 average rating, 13 reviews
Cottage in Massachusetts
Historic 1810 Farmhouse - Fully Renovated
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.95 out of 5 average rating, 149 reviews
Home in Massachusetts
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 16 reviews
Home in Massachusetts
Quiet, 3 Bedroom, one Story Home on 17 acres.
3 bedrooms, 3 beds, 2 bathrooms
8–15 Aug
Bed and breakfast in Massachusetts
Standard Suite with a Patio at Shaker Mill Inn
1 bedroom, 3 beds, 1 bathroom
23–28 Jul
5.0 out of 5 average rating, 10 reviews
Bed and breakfast in Massachusetts
Deluxe Suite with a Patio Pets allowed
1 bedroom, 2 beds, 1 bathroom
8–13 Jul
5.0 out of 5 average rating, 3 reviews
Bed and breakfast in Massachusetts
Deluxe Suite with a Balcony Pets allowed
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Home in Massachusetts
Secluded Chic Mountain Chalet near Tanglewood
3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
4.93 out of 5 average rating, 54 reviews
Bed and breakfast in Massachusetts
Standard Suite at Shaker Mill Inn
1 bedroom, 2 queen beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Home in Massachusetts
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Barn in Massachusetts
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 39 reviews
Guest house in New York
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
4–9 Jul
5.0 out of 5 average rating, 4 reviews
Cabin in Massachusetts
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, 136 reviews
Home in New York
Private Pool Retreat w/ Deck Near the Berkshires
6 bedrooms, 9 beds, 3.5 bathrooms
29 Aug – 3 Sept
New place to stay
Home in New York
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 13 reviews
Home in Massachusetts
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 24 reviews
Home in Massachusetts
Berkshires Forest Retreat with Hot Tub
3 bedrooms, 3 beds, 2 bathrooms
4–9 Sept
4.99 out of 5 average rating, 81 reviews