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Search results; Over 1,000 homes in Stephentown

Top guest favourite
Guest house in Stephentown
Dog Friendly Studio
Studio, 1 bed, 1 private bathroom
11–16 Sept
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5.0 out of 5 average rating, 483 reviews
Home in Stephentown
Ioka Valley Farm's Little Farm House
3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
New place to stay
Guest favourite
Flat in Stephentown
Cozy 2-Bedroom Vacation Apartment
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 109 reviews
Guest favourite
Flat in Stephentown
2 Bed Berkshire Getaway @ Stephentown Hotel
2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 50 reviews
Guest favourite
Flat in Stephentown
Berkshires Apartment @ the Stephentown Hotel
3 beds, 1 bathroom
16–21 Aug
4.83 out of 5 average rating, 30 reviews
Guest favourite
Home in Stephentown
Fam-Friendly Berkshire Views and Private Swim Pond
3 bedrooms, 4 beds, 1.5 bathrooms
23–28 Aug
4.89 out of 5 average rating, 35 reviews
Home in Stephentown
13BR Retreat | Heated Pool, Hot Tub + Game Room
13 bedrooms, 26 beds, 12.5 bathrooms
7–12 Sept
Top guest favourite
Cabin in Stephentown
Stylish Mountain Cabin Close To Cherry Plain Park
3 bedrooms, 5 beds, 2 bathrooms
18–23 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Flat in Stephentown
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
5 bedrooms, 5 beds, 3 bathrooms
16–21 Aug
4.89 out of 5 average rating, 18 reviews
Guest favourite
Home in New Lebanon
Unplug in the Berkshires | Your Summer Escape
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.91 out of 5 average rating, 68 reviews
Guest favourite
Home in Stephentown
Lovely Secluded Berkshire MTN View 3BR Near Skiing
3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
4.81 out of 5 average rating, 209 reviews
Guest favourite
Cabin in East Nassau
The Kinderhook Cabin on the Kinderhook creek.
3 bedrooms, 6 beds, 1 bathroom
31 Aug – 5 Sept
4.94 out of 5 average rating, 52 reviews
Top guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Petersburgh
Beautiful Rustic A-Frame
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
25–30 Sept
4.99 out of 5 average rating, 325 reviews
Top guest favourite
Home in New Lebanon
The old sawmill from 1771
1 bedroom, 2 beds, 2 bathrooms
16–21 Aug
4.99 out of 5 average rating, 383 reviews
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Cottage in Williamstown
Cute Cozy Comfy Cottage in the Berkshires
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
4.89 out of 5 average rating, 208 reviews