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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, 46 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
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
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
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
Guest favourite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 153 reviews
Guest favourite
Home in West Stockbridge
Modern Log Cabin w/Pool & Views By Evergreen Home
4 bedrooms, 5 beds, 3.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 11 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 Canaan
Crossings Cottage
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 90 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
25–30 Sept
4.99 out of 5 average rating, 325 reviews
Top guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 13 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, 171 reviews
Top guest favourite
Cabin in Spencertown
Wake Up in the Woods, A Summer Reset Upstate
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.97 out of 5 average rating, 31 reviews
Top 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
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
9–14 Aug
4.91 out of 5 average rating, 169 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 188 reviews
Top guest favourite
Barn in Town of Hillsdale
Blue Door Barn - Pond and Sweeping Views
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.85 out of 5 average rating, 158 reviews
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 queen beds, 2.5 bathrooms
13–18 Sept
4.95 out of 5 average rating, 185 reviews