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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
Superhost
Home in Richmond
Berkshires Chalet Mins to Tanglewood/Lenox
4 bedrooms, 7 beds
13–18 Jul
Guest favourite
Home in Richmond
Classic New England Home with a Swimming Pool
4 bedrooms, 5 beds
22–27 Aug
4.92 out of 5 average rating, 13 reviews
Home in Richmond
Richmond Pond All Season Retreat
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Richmond
Bucolic Pet Friendly Oasis | 10 min to Tanglewood
4 bedrooms, 4 beds
3–9 Aug
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Richmond
Escape to The Berkshires w/Pool by Evergreen Home
4 bedrooms, 5 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Home in Richmond
"Hemlock Shadow" near Tanglewood on Six Acres
4 bedrooms, 4 beds
29 Aug – 3 Sept
4.95 out of 5 average rating, 19 reviews
Guest favourite
Cottage in Pittsfield
Charming lakeview cottage w/ kayaks, Richmond Pond
3 bedrooms, 4 beds
3–8 Sept
4.8 out of 5 average rating, 51 reviews
Top guest favourite
Guest suite in Richmond
Berkshire Mountain Retreat
1 bedroom, 2 beds
2–7 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Home in Richmond
Gated Mansion, Heated Pool, Mini Gym- Sleeps 11!
5 bedrooms, 9 beds
14–19 Mar
5.0 out of 5 average rating, 10 reviews
Home in Richmond
1 Mi to Vineyard: Serene Berkshires Country Escape
4 bedrooms, 4 beds
30 Sept – 5 Oct
4.5 out of 5 average rating, 6 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed
23–28 Aug
4.99 out of 5 average rating, 314 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds
23–28 Aug
4.96 out of 5 average rating, 199 reviews
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds
26–31 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Guest suite in Lenox
T’Other House
1 bedroom, 1 queen bed
12–17 Jul
4.97 out of 5 average rating, 237 reviews
Home in New Lebanon
Above the Clouds Mountain Retreat
3 bedrooms, 3 beds
14–19 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
9–14 Aug
4.91 out of 5 average rating, 316 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed
19–24 Jul
4.97 out of 5 average rating, 599 reviews