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Search results; Over 1,000 homes in Richmond

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Guest favourite
Home in Richmond
Classic New England Home with direct trail access
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.95 out of 5 average rating, 21 reviews
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Guest favourite
Home in Richmond
Berkshires Chalet Mins to Tanglewood/Lenox
4 bedrooms, 7 beds, 3 bathrooms
1–6 Oct
4.83 out of 5 average rating, 6 reviews
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Guest favourite
Home in Richmond
Bucolic Pet Friendly Oasis | 10 min to Tanglewood
4 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.97 out of 5 average rating, 33 reviews
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Guest favourite
Guest suite in Richmond
Berkshires/Pet Friendly/Tanglewood/Private Ranch
2 bedrooms, 3 queen beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 207 reviews
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Guest favourite
Home in Richmond
Richmond Pond All Season Retreat
3 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 6 reviews
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Home in Richmond
1 Mi to Vineyard: Serene Berkshires Country Escape
4 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.38 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Pittsfield
Berkshires Colonial on 2 Acres by Evergreen Home
4 bedrooms, 9 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 57 reviews
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Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 38 reviews
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Guest favourite
Home in Richmond
Minutes to Tanglewood with Massive Backyard
5 bedrooms, 7 beds, 2.5 bathrooms
1–6 Oct
4.92 out of 5 average rating, 39 reviews
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Guest favourite
Cottage in Pittsfield
Charming lakeview cottage w/ kayaks, Richmond Pond
3 bedrooms, 4 beds, 1 bathroom
19–24 Oct
4.83 out of 5 average rating, 58 reviews
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Home in Richmond
Josiah Loomis 1832 Homestead
3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.57 out of 5 average rating, 83 reviews
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Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Dec
4.97 out of 5 average rating, 208 reviews
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Top guest favourite
Cabin in East Nassau
Fall Foliage Luxury Cabin & View Autumn Adventures
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 110 reviews
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Guest favourite
Home in Canaan
The Little Yellow Door
5 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
4.96 out of 5 average rating, 53 reviews
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Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.94 out of 5 average rating, 16 reviews
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Top guest favourite
Home in Canaan
Secluded Mountain and Lake View in Canaan, NY
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 45 reviews
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Guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 26 reviews
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Superhost
Chalet in Lenox
Modern Chalet Near Tanglewood & Downtown Lenox
3 bedrooms, 4 beds, 3 bathrooms
19–24 Oct
4.87 out of 5 average rating, 46 reviews