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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 queen beds, 1 bathroom
30 Aug – 4 Sept
4.94 out of 5 average rating, 205 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
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
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
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
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, 327 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
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
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 618 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
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.96 out of 5 average rating, 228 reviews
Guest favourite
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
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
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 313 reviews
Home in Lenox
Lenox cottage 1 mile from town center 2 bed 2 bath
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
New place to stay
Top guest favourite
Flat in East Chatham
Bennett Abode
1 bedroom, 1 double bed, 1.5 bathrooms
31 Aug – 5 Sept
4.96 out of 5 average rating, 181 reviews
Top guest favourite
Cottage in New Lebanon
The Writer's Cottage
2 bedrooms, 2 beds, 1 bathroom
10–15 Sept
4.94 out of 5 average rating, 214 reviews
Top guest favourite
Home in Canaan
Cozy modern Berkshire home with sauna & fire pit
3 bedrooms, 3 beds, 3 bathrooms
8–13 Sept
4.97 out of 5 average rating, 62 reviews