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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, 470 reviews
Top guest favourite
Flat in Stephentown
Cozy 2-Bedroom Vacation Apartment
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 104 reviews
Guest favourite
Flat in Stephentown
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
4.85 out of 5 average rating, 75 reviews
Guest favourite
Home in Stephentown
Fam-Friendly Berkshire Views and Private Swim Pond
3 bedrooms, 4 beds, 1.5 bathrooms
19–24 Jul
4.89 out of 5 average rating, 35 reviews
Home in New Lebanon
Above the Clouds Mountain Retreat
3 bedrooms, 3 beds, 4 bathrooms
6–11 Jul
New place to stay
Top guest favourite
Cabin in Stephentown
Stylish Mountain Cabin Close To Cherry Plain Park
3 bedrooms, 5 beds, 2 bathrooms
4–9 Aug
5.0 out of 5 average rating, 26 reviews
Home in Stephentown
13BR Retreat | Heated Pool, Hot Tub + Game Room
13 bedrooms, 26 beds, 12.5 bathrooms
8–13 Jul
Guest favourite
Flat in Stephentown
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
5 bedrooms, 5 beds, 3 bathrooms
5–10 Jul
4.88 out of 5 average rating, 17 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, 3 reviews
Top guest favourite
Cabin in Sand Lake
"The Cabin" - Cozy & Rustic Home (Averill Park)
3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 307 reviews
Top guest favourite
Chalet in Averill Park
A Hidden Sparrow
4 bedrooms, 4 beds, 1.5 bathrooms
6–11 Jul
4.94 out of 5 average rating, 94 reviews
Top guest favourite
Home in New Lebanon
The old sawmill from 1771
1 bedroom, 2 beds, 2 bathrooms
1–6 Sept
4.99 out of 5 average rating, 381 reviews
Flat in Cheshire
4 Bedrooms first floor home.
4 bedrooms, 6 beds, 1.5 bathrooms
4–9 Jul
Top guest favourite
Home in Hudson
Chic Hudson Farmhouse w/ Fireplace & Porch
3 bedrooms, 3 beds, 1.5 bathrooms
2–7 Aug
4.97 out of 5 average rating, 117 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 196 reviews
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
New place to stay
Superhost
Cabin in Chatham
Camp Jack | Explorer A-Frame + Private Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
15–20 Jul
New place to stay
Top guest favourite
Flat in New Lebanon
Loft Space above Brewery
1 bedroom, 3 beds, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 28 reviews