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Search results; Over 1,000 homes in Richmond

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, 201 reviews
Home in Richmond
Berkshires Chalet Mins to Tanglewood/Lenox
4 bedrooms, 7 beds, 3 bathrooms
13–18 Jul
Top guest favourite
Home in West Stockbridge
Secluded Chic Mountain Chalet near Tanglewood
4.93 out of 5 average rating, 55 reviews, 3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Guest favourite
Home in Richmond
Classic New England Home with a Swimming Pool
4.92 out of 5 average rating, 13 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
22–27 Aug
Guest favourite
Home in Richmond
Bucolic Pet Friendly Oasis | 10 min to Tanglewood
4.96 out of 5 average rating, 28 reviews, 4 bedrooms, 4 beds, 2 bathrooms
3–9 Aug
Top guest favourite
Home in Pittsfield
Berkshires Colonial on 2 Acres by Evergreen Home
5.0 out of 5 average rating, 55 reviews, 4 bedrooms, 9 beds, 2.5 bathrooms
16–21 Aug
Superhost
Home in Lenox
Belden Farm - WALK to Tanglewood !
New place to stay, 6 bedrooms, 7 beds, 3 bathrooms
2–7 Sept
Top guest favourite
Home in Richmond
"Hemlock Shadow" near Tanglewood on Six Acres
4.95 out of 5 average rating, 19 reviews, 4 bedrooms, 4 beds, 3 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Canaan
Cozy modern Berkshire home with sauna & fire pit
4.96 out of 5 average rating, 57 reviews, 3 bedrooms, 3 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Home in West Stockbridge
Berkshires-Enjoy The Peak, private home
4.94 out of 5 average rating, 104 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept
Guest favourite
Home in Pittsfield
Friendly Hills | Passive Home • EV Charger
4.91 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
Guest favourite
Cottage in Pittsfield
Charming lakeview cottage w/ kayaks, Richmond Pond
4.8 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 1 bathroom
3–8 Sept
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
4.96 out of 5 average rating, 199 reviews, 2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
Home in Richmond
Richmond Pond All Season Retreat
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Guest suite in Richmond
Berkshire Mountain Retreat
4.96 out of 5 average rating, 47 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Sept
Top guest favourite
Home in Canaan
Secluded Mountain and Lake View in Canaan, NY
4.95 out of 5 average rating, 38 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
28 Aug – 2 Sept
Guest favourite
Home in Richmond
Escape to The Berkshires w/Pool by Evergreen Home
4.97 out of 5 average rating, 34 reviews, 4 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 314 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug