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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
7–12 Sept
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4.94 out of 5 average rating, 207 reviews
Guest favourite
Home in Richmond
Bucolic Pet Friendly Oasis | 10 min to Tanglewood
4 bedrooms, 4 beds, 2 bathrooms
7–13 Sept
4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in Richmond
Classic New England Home with a Swimming Pool
4 bedrooms, 5 beds, 2.5 bathrooms
6–11 Sept
4.95 out of 5 average rating, 19 reviews
Guest favourite
Home in Richmond
Berkshires Chalet Mins to Tanglewood/Lenox
4 bedrooms, 7 beds, 3 bathrooms
19–24 Sept
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Home in West Stockbridge
Secluded Chic Mountain Chalet near Tanglewood
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.93 out of 5 average rating, 58 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, 63 reviews
Top guest favourite
Guest suite in Richmond
Berkshire Mountain Retreat
1 bedroom, 2 beds, 1 bathroom
12–17 Oct
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Home in West Stockbridge
Berkshires-Enjoy The Peak, private home
3 bedrooms, 3 beds, 2.5 bathrooms
30 Oct – 4 Nov
4.95 out of 5 average rating, 111 reviews
Guest favourite
Cottage in Pittsfield
Charming lakeview cottage w/ kayaks, Richmond Pond
3 bedrooms, 4 beds, 1 bathroom
8–13 Sept
4.82 out of 5 average rating, 57 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
4.97 out of 5 average rating, 206 reviews
Guest favourite
Home in Richmond
Richmond Pond All Season Retreat
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Pittsfield
Modern, Renovated Lakefront Escape
4 bedrooms, 6 beds, 3 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Home in Stockbridge
Relaxing Berkshire Retreat with Lake Access
3 bedrooms, 4 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Flat in Lenox
Historical Housatonic Street Building
2 bedrooms, 1 king bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Richmond
Sunshine Cottage
1 bedroom, 1 queen bed, 1 bathroom
1–6 Jan
4.94 out of 5 average rating, 32 reviews
Guest favourite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 154 reviews
Top guest favourite
Home in Canaan
Relax and Rejuvenate at Fox Hollow Cottage
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Pittsfield
Berkshires Colonial on 2 Acres by Evergreen Home
4 bedrooms, 9 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 57 reviews
Guest favourite
Home in Pittsfield
Friendly Hills | Passive Home • EV Charger
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.91 out of 5 average rating, 46 reviews