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Search results; Over 1,000 homes in Richmond

Top guest favourite
Guest suite in Richmond
Berkshire Mountain Retreat
1 bedroom, 2 beds, 1 private bathroom
21–26 Sept
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4.96 out of 5 average rating, 49 reviews
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
30 Aug – 4 Sept
4.97 out of 5 average rating, 29 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, 201 reviews
Home in Richmond
Berkshires Chalet Mins to Tanglewood/Lenox
4 bedrooms, 7 beds, 3 bathrooms
11–16 Aug
4.75 out of 5 average rating, 4 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, 615 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, 32 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
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, 312 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
4.86 out of 5 average rating, 28 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
Top guest favourite
Cabin in Chatham
Rustic Secluded Cabin near Berkshires. *wood stove
4 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
4.92 out of 5 average rating, 142 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
Home in Canaan
Crossings Cottage
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 90 reviews
Guest favourite
Earthen home in Canaan
Guest Eco Studio w/ Pool & Sauna on 100+ Acres
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in East Chatham
Bennett Abode
1 bedroom, 1 double bed, 1.5 bathrooms
6–11 Sept
4.96 out of 5 average rating, 179 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 88 reviews
Home in New Lebanon
Spacious 4BR Summer Escape | Queechy Lake Passes
4 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.8 out of 5 average rating, 20 reviews