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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 Apt minutes to Jiminy Peak Ski
4.85 out of 5 average rating, 75 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
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
Home in Stephentown
13BR Retreat | Heated Pool, Hot Tub + Game Room
13 bedrooms, 26 beds, 12.5 bathrooms
8–13 Jul
Home in Stephentown
Ioka Valley Farm's Little Farm House
New place to stay, 3 bedrooms, 4 beds, 1 bathroom
7–12 Jul
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
Top guest favourite
Flat in New Lebanon
Folk Art Studio: 1-bedroom near the Berkshires
5.0 out of 5 average rating, 30 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Flat in New Lebanon
Airy apartment at the old boarding house
4.97 out of 5 average rating, 117 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Aug – 2 Sept
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
7–12 Jul
Superhost
Home in Stephentown
The entire Stephentown Hotel! 28 person occupancy
5.0 out of 5 average rating, 3 reviews, 10 bedrooms, 10 beds, 6 bathrooms
16–21 Aug
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
Top guest favourite
Cottage in New Lebanon
The Writer's Cottage
4.94 out of 5 average rating, 212 reviews, 2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Apartment in Hancock
SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1
4.94 out of 5 average rating, 98 reviews, 3 bedrooms, 7 beds, 2 bathrooms
22–27 Jul
Guest favourite
Apartment in Hancock
SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
4.96 out of 5 average rating, 57 reviews, 2 bedrooms, 6 beds, 2 bathrooms
7–12 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
19–24 Jul
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
4.94 out of 5 average rating, 35 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
4.96 out of 5 average rating, 199 reviews, 2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul