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Search results; Over 1,000 homes in Stephentown

Superhost
Cabin in Stephentown
Rustic Cabin | Barrel Sauna | Private Pond
2 bedrooms, 2 beds, 1 shared bathroom
27 Jul – 1 Aug
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4.86 out of 5 average rating, 312 reviews
Guest favourite
Flat in Stephentown
2 Bed Berkshire Getaway @ Stephentown Hotel
4.96 out of 5 average rating, 50 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
Guest favourite
Flat in Stephentown
Cozy 2-Bedroom Vacation Apartment
4.99 out of 5 average rating, 107 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Top guest favourite
Guest house in Stephentown
Dog Friendly Studio
5.0 out of 5 average rating, 479 reviews, 1 bed, 1 bathroom
26–31 Jul
Guest favourite
Home in Stephentown
Fam-Friendly Berkshire Views and Private Swim Pond
4.89 out of 5 average rating, 35 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
22–27 Jul
Home in Stephentown
13BR Retreat | Heated Pool, Hot Tub + Game Room
13 bedrooms, 26 beds, 12.5 bathrooms
9–14 Aug
Guest favourite
Flat in Stephentown
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
4.89 out of 5 average rating, 18 reviews, 5 bedrooms, 5 beds, 3 bathrooms
26–31 Jul
Top guest favourite
Cabin in Stephentown
Stylish Mountain Cabin Close To Cherry Plain Park
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 5 beds, 2 bathrooms
18–23 Aug
Home in Stephentown
Ioka Valley Farm's Little Farm House
New place to stay, 3 bedrooms, 4 beds, 1 bathroom
21–26 Jul
Guest favourite
Flat in Stephentown
Berkshires Apartment @ the Stephentown Hotel
4.83 out of 5 average rating, 29 reviews, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Hancock
Grand 6BR Home by Jiminy | Hike • Hot Tub • Games
4.97 out of 5 average rating, 58 reviews, 6 bedrooms, 14 beds, 5.5 bathrooms
2–7 Aug
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
Home in Petersburgh
Beautiful Rustic A-Frame
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Aug
Guest favourite
Cabin in East Nassau
The Kinderhook Cabin on the Kinderhook creek.
4.94 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 311 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Holiday home in Stephentown
Quiet, peaceful wooded setting.
4.97 out of 5 average rating, 31 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Oct
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 317 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Sept
Guest favourite
Cottage in Williamstown
Cute Cozy Comfy Cottage in the Berkshires
4.89 out of 5 average rating, 207 reviews, 1 bedroom, 2 beds, 1 bathroom
29 Jul – 3 Aug
Guest favourite
Home in New Lebanon
Unplug in the Berkshires | Your Summer Escape
4.92 out of 5 average rating, 66 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug