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Search results; Over 1,000 homes in Richmond

Top guest favourite
Guest suite in Richmond
Berkshires/Pet Friendly/Tanglewood/Private Ranch
2 bedrooms, 3 beds, 1 private bathroom
30 Aug – 4 Sept
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4.94 out of 5 average rating, 205 reviews
Guest favourite
Home in Richmond
Classic New England Home with a Swimming Pool
4 bedrooms, 5 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 16 reviews
Guest favourite
Home in Richmond
Bucolic Pet Friendly Oasis | 10 min to Tanglewood
4 bedrooms, 4 beds, 2 bathrooms
3–8 Sept
4.97 out of 5 average rating, 30 reviews
Guest favourite
Home in Richmond
Richmond Pond All Season Retreat
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Home in Richmond
Berkshires Chalet Mins to Tanglewood/Lenox
4 bedrooms, 7 beds, 3 bathrooms
21–26 Sept
4.8 out of 5 average rating, 5 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Richmond
Minutes to Tanglewood with Massive Backyard
5 bedrooms, 7 beds, 2.5 bathrooms
23–28 Aug
4.92 out of 5 average rating, 39 reviews
Top guest favourite
Guest suite in Richmond
Berkshire Mountain Retreat
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
4.96 out of 5 average rating, 49 reviews
Guest favourite
Home in Richmond
Escape to The Berkshires w/Pool by Evergreen Home
4 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 35 reviews
Home in Pittsfield
3 Acres, Mtn Views, Hot Tub, Steps to Winery
3 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
New place to stay
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, 190 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 202 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 324 reviews
Guest favourite
Cottage in Pittsfield
Charming lakeview cottage w/ kayaks, Richmond Pond
3 bedrooms, 4 beds, 1 bathroom
3–8 Sept
4.82 out of 5 average rating, 55 reviews
Top guest favourite
Tiny home in Chatham
Boutique TINY home+private HOT TUB-walk to Main St
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 371 reviews
Guest favourite
Cabin in Lenox
Timpani Corners | Private Pond • AC
3 bedrooms, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Richmond
"Hemlock Shadow" near Tanglewood on Six Acres
4 bedrooms, 4 beds, 3 bathrooms
29 Aug – 3 Sept
4.95 out of 5 average rating, 20 reviews
Home in Lenox
The Gardener's Cottage 1893 at Ventfort Hall
2 bedrooms, 2 queen beds, 1.5 bathrooms
22–27 Aug
New place to stay
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
3 bedrooms, 5 beds, 2 bathrooms
3–8 Sept
4.98 out of 5 average rating, 64 reviews