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Search results; Over 1,000 homes in New Ashford

Guest favourite
Home in New Ashford
Rosecroft, Historic Home, Greylock Valley Estate
8 bedrooms, 8 beds, 3 private bathrooms
30 Aug – 4 Sept
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4.92 out of 5 average rating, 229 reviews
Guest favourite
Cabin in New Ashford
Charming 2BR Berkshire Cabin
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.8 out of 5 average rating, 5 reviews
Guest favourite
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.8 out of 5 average rating, 96 reviews
Guest favourite
Cabin in New Ashford
Rustic Cabin with Wood Fireplace
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 23 reviews
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, 7 reviews
Guest favourite
Home in Williamstown
Bridy's View
3 bedrooms, 5 beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Pownal
Cozy Vermont mini-house
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 299 reviews
Top guest favourite
Cabin in Florida
The Greylock Cabin
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 81 reviews
Top guest favourite
Home in Adams
Mount Greylock View Retreat,3 bedroom,2 1/2 bath.
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
4.94 out of 5 average rating, 84 reviews
Top guest favourite
Flat in Williamstown
House on the Town Green
2 bedrooms, 2 beds, 1 bathroom
18–23 Aug
4.98 out of 5 average rating, 148 reviews
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
20–25 Nov
4.96 out of 5 average rating, 53 reviews
Top guest favourite
Flat in North Adams
Steps to MoCA: 2bd + SAUNA!
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 724 reviews
Top guest favourite
Home in Petersburgh
Beautiful Rustic A-Frame
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Barn in Williamstown
Cozy barn apartment on the river
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.97 out of 5 average rating, 343 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.96 out of 5 average rating, 228 reviews
Guest favourite
Townhouse in Cheshire
4 Bedrooms first floor home.
4 bedrooms, 4 beds, 1.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Loft in Williamstown
Vacation Rental Home in the Berkshires!
1 king bed, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 46 reviews
Top guest favourite
Flat in Williamstown
Chic Downtown Studio, Perfect for College Weekends
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
4.95 out of 5 average rating, 370 reviews