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Search results; Over 1,000 homes in New Ashford

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Superhost
Hotel in New Ashford
Springs Motel Honeymoon Suite
1 bedroom, 1 bed, 2 private bathrooms
4–9 Oct
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Guest favourite
Home in New Ashford
Rosecroft, Historic Home, Greylock Valley Estate
8 bedrooms, 8 beds, 3 bathrooms
4–9 Oct
4.92 out of 5 average rating, 233 reviews
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Superhost
Cabin in New Ashford
Rustic Cabin with Wood Fireplace
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 25 reviews
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Guest favourite
Home in Williamstown
Charming Berkshire Retreat-Minutes to Williamstown
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Cabin in New Ashford
Charming 2BR Berkshire Cabin
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.83 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Adams
Beautiful Victorian. The heart of the Berkshires.
5 bedrooms, 6 beds, 2 bathrooms
17–22 Sept
4.91 out of 5 average rating, 149 reviews
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Top guest favourite
Home in Williamstown
Elegant Mountain View Retreat By Evergreen Home
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 72 reviews
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Flat in Williamstown
Sugar House Farm Stay
2 bedrooms, 2 beds, 1 bathroom
19–24 Sept
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Top guest favourite
Home in Lanesborough
Berkshire Mountain House
4 bedrooms, 5 beds, 3 bathrooms
17–22 Sept
5.0 out of 5 average rating, 43 reviews
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Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 238 reviews
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Guest favourite
Home in Hancock
Lovely Home in the Berkshires
3 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
4.89 out of 5 average rating, 18 reviews
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Guest favourite
Home in Hancock
Family Lodge at Jiminy Peak - Pools & Adventure
4 bedrooms, 9 beds, 3 bathrooms
20–25 Sept
4.93 out of 5 average rating, 61 reviews
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Home in North Adams
Scandinavian Berkshire Cottage Near MASS MoCA
3 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
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Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 27 reviews
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Top guest favourite
Cottage in Williamstown
Charming Williamstown Cottage
3 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.99 out of 5 average rating, 147 reviews
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Top guest favourite
Flat in North Adams
Charming Art Filled Apartment
3 bedrooms, 3 queen beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 199 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
27 Sept – 2 Oct
4.97 out of 5 average rating, 109 reviews
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Top guest favourite
Home in Adams
Cozy Home In The Berkshires, Pet Friendly!
3 bedrooms, 3 beds, 1.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 11 reviews