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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, 490 reviews
Guest favourite
Flat in Stephentown
2 Bed Berkshire Getaway @ Stephentown Hotel
2 bedrooms, 4 beds, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 50 reviews
Guest favourite
Flat in Stephentown
Berkshires Apartment @ the Stephentown Hotel
3 beds, 1 bathroom
7–13 Sept
4.84 out of 5 average rating, 31 reviews
Home in Stephentown
13BR Retreat | Heated Pool, Hot Tub + Game Room
13 bedrooms, 26 beds, 12.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Stephentown
Cozy 2-Bedroom Vacation Apartment
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 110 reviews
Home in Stephentown
Farm House with Free passes to Ioka Valley Farm
3 bedrooms, 4 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Stephentown
The entire Stephentown Hotel! 28 person occupancy
10 bedrooms, 10 beds, 6 bathrooms
7–13 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Stephentown
Fam-Friendly Berkshire Views and Private Swim Pond
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.89 out of 5 average rating, 36 reviews
Guest favourite
Flat in Stephentown
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
5 bedrooms, 5 beds, 3 bathrooms
7–13 Sept
4.89 out of 5 average rating, 18 reviews
Top guest favourite
Cabin in Stephentown
Stylish Mountain Cabin Close To Cherry Plain Park
3 bedrooms, 5 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 28 reviews
Home in Stephentown
Secluded Upstate House, 7 Acres Near Jiminy Peak
3 bedrooms, 2 beds, 2.5 bathrooms
17–22 Oct
New place to stay
Top guest favourite
Holiday home in Stephentown
Quiet, peaceful wooded setting.
1 bedroom, 1 queen bed, 1 bathroom
20–25 Oct
4.97 out of 5 average rating, 31 reviews
Guest favourite
Home in Stephentown
Converted Barn w/pond on 120 Acres
5 bedrooms, 7 beds, 2.5 bathrooms
8–13 Sept
4.98 out of 5 average rating, 48 reviews
Guest favourite
Home in New Lebanon
Unplug in the Berkshires | Your Summer Escape
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.91 out of 5 average rating, 70 reviews
Guest favourite
Home in Hancock
Family Lodge at Jiminy Peak - Pools & Adventure
4 bedrooms, 9 beds, 3 bathrooms
7–12 Sept
4.93 out of 5 average rating, 59 reviews
Top guest favourite
Home in Hancock
Grand 6BR Home by Jiminy | Hike • Hot Tub • Games
6 bedrooms, 14 beds, 5.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 64 reviews
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Townhouse in Hancock
LuNo - Relaxing Ski and Culture Berkshires Escape
3 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 14 reviews