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Search results; Over 1,000 homes in Stephentown

Superhost
Home in Stephentown
A Magic Spot: Booking year round.
4 bedrooms, 5 beds, 2 private bathrooms
22–27 Aug
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4.82 out of 5 average rating, 91 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
Cozy 2-Bedroom Vacation Apartment
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 109 reviews
Home in Stephentown
Ioka Valley Farm's Little Farm House
3 bedrooms, 4 beds, 1 bathroom
15–20 Aug
New place to stay
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
Top guest favourite
Guest house in Stephentown
Dog Friendly Studio
1 queen bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 484 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, 36 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
Top guest favourite
Cabin in Stephentown
Stylish Mountain Cabin Close To Cherry Plain Park
3 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
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
Superhost
Home in Stephentown
The entire Stephentown Hotel! 28 person occupancy
10 bedrooms, 10 beds, 6 bathrooms
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Chalet in Averill Park
A Hidden Sparrow
4 bedrooms, 4 beds, 1.5 bathrooms
24–29 Aug
4.94 out of 5 average rating, 101 reviews
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 Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
4.95 out of 5 average rating, 38 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
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
Top guest favourite
Cabin in Petersburg
Cozy Retreat in the Trees
2 bedrooms, 4 beds, 1 bathroom
6–11 Sept
4.94 out of 5 average rating, 280 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
Cottage in Nassau
Lemongrass Cottage!
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 87 reviews