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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
30 Aug – 4 Sept
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4.94 out of 5 average rating, 204 reviews
Top guest favourite
Guest suite in Richmond
Berkshire Mountain Retreat
1 bedroom, 2 beds
30 Aug – 4 Sept
4.96 out of 5 average rating, 48 reviews
Guest favourite
Home in Richmond
Richmond Pond All Season Retreat
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Home in Richmond
Berkshires Chalet Mins to Tanglewood/Lenox
4 bedrooms, 7 beds
11–16 Aug
4.75 out of 5 average rating, 4 reviews
Home in Richmond
1 Mi to Vineyard: Serene Berkshires Country Escape
4 bedrooms, 4 beds
30 Sept – 5 Oct
4.29 out of 5 average rating, 7 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, 35 reviews
Guest favourite
Home in Richmond
Classic New England Home with a Swimming Pool
4 bedrooms, 5 beds
30 Aug – 4 Sept
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Canaan
Crossings Cottage
2 bedrooms, 2 beds
13–18 Sept
4.97 out of 5 average rating, 90 reviews
Guest favourite
Home in Richmond
Bucolic Pet Friendly Oasis | 10 min to Tanglewood
4 bedrooms, 4 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Berkshires
1 king bed
23–28 Aug
4.88 out of 5 average rating, 130 reviews
Top guest favourite
Guest house in West Stockbridge
Guest House 15 mins to Tanglewood
2 beds
14–19 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Flat in Lenox
Main Street Delight One Bedroom Apartment
1 bedroom, 1 queen bed
23–28 Oct
4.98 out of 5 average rating, 90 reviews
Guest favourite
Guest house in Canaan
Airy cottage with meadow views in The Berkshires
1 bedroom, 3 beds
8–13 Sept
4.93 out of 5 average rating, 211 reviews
Guest favourite
Room in Lenox
Cozy Private room w/Private bath, Lenoxdale, MA
1 double bed
9–14 Aug
4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in Richmond
Berkshire Designer Cottage
1 bedroom, 1 queen bed
18–23 Oct
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Pittsfield
Friendly Hills | Passive Home • EV Charger
3 bedrooms, 4 beds
14–19 Sept
4.9 out of 5 average rating, 40 reviews
Guest favourite
Home in Richmond
Richmond Ranch w/ Hot Tub by Evergreen Home
3 bedrooms, 4 beds
2–7 Jan
4.88 out of 5 average rating, 24 reviews
Top guest favourite
Place to stay in Canaan
Serene Berkshire Room with breakfast
1 bedroom, 1 queen bed
13–18 Aug
4.94 out of 5 average rating, 104 reviews
Guest favourite
Cabin in Lenox
Timpani Corners | Private Pond • AC
3 bedrooms, 3 beds
10–15 Sept
5.0 out of 5 average rating, 5 reviews