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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
26–31 Jul
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5.0 out of 5 average rating, 474 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
12–17 Jul
Guest favourite
Flat in Stephentown
Cozy 2-Bedroom Vacation Apartment
5.0 out of 5 average rating, 104 reviews, 2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
Top guest favourite
Cabin in Stephentown
Stylish Mountain Cabin Close To Cherry Plain Park
5.0 out of 5 average rating, 27 reviews, 3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
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
19–24 Jul
Guest favourite
Flat in Stephentown
Berkshires Apartment @ the Stephentown Hotel
4.82 out of 5 average rating, 28 reviews, 3 beds, 1 bathroom
16–21 Aug
Guest favourite
Flat in Stephentown
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
4.88 out of 5 average rating, 17 reviews, 5 bedrooms, 5 beds, 3 bathrooms
12–17 Jul
Home in Stephentown
13BR Retreat | Heated Pool, Hot Tub + Game Room
13 bedrooms, 26 beds, 12.5 bathrooms
8–13 Jul
Cabin in Johnsonville
The Mountain Cabin at One Trick Pony Ranch
New place to stay, 1 bedroom, 1 bed, 1 bathroom
8–13 Jul
Guest favourite
Home in Stephentown
Lovely Secluded Berkshire MTN View 3BR Near Skiing
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
8–13 Jul
Top guest favourite
Cabin in Sand Lake
"The Cabin" - Cozy & Rustic Home (Averill Park)
5.0 out of 5 average rating, 49 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–13 Jul
Guest favourite
Cottage in Williamstown
Cute Cozy Comfy Cottage in the Berkshires
4.89 out of 5 average rating, 206 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Jul
Top guest favourite
Flat in Petersburg
The Beer Diviner Brewery Apartment
4.9 out of 5 average rating, 223 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Tiny home in Stephentown
Tiny House Glamping on Peaceful Farm
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Flat in Pittsfield
Marie's Place
4.91 out of 5 average rating, 316 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
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
Cottage in Nassau
Lemongrass Cottage!
4.96 out of 5 average rating, 77 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Flat in New Lebanon
Loft Space above Brewery
5.0 out of 5 average rating, 30 reviews, 1 bedroom, 3 beds, 1 bathroom
13–18 Sept