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Search results; Over 1,000 homes in Stephentown

Superhost
Cabin in Stephentown
Rustic Cabin | Barrel Sauna | Private Pond
2 bedrooms, 2 beds, 1 shared bathroom
20–25 Sept
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4.86 out of 5 average rating, 313 reviews
Guest favourite
Flat in Stephentown
2 Bed Berkshire Getaway @ Stephentown Hotel
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 50 reviews
Guest favourite
Flat in Stephentown
Berkshires Apartment @ the Stephentown Hotel
3 beds, 1 bathroom
20–25 Sept
4.84 out of 5 average rating, 32 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, 112 reviews
Home in Stephentown
13BR Retreat | Heated Pool, Hot Tub + Game Room
13 bedrooms, 26 beds, 12.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Stephentown
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
5 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
4.9 out of 5 average rating, 20 reviews
Top guest favourite
Guest house in Stephentown
Dog Friendly Studio
1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 492 reviews
Superhost
Home in Stephentown
The entire Stephentown Hotel! 28 person occupancy
10 bedrooms, 10 beds, 6 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Home in Stephentown
Ioka's Little Farm House
3 bedrooms, 4 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 4 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
Home in New Lebanon
The old sawmill from 1771
1 bedroom, 2 beds, 2 bathrooms
19–24 Oct
4.99 out of 5 average rating, 387 reviews
Guest favourite
Home in East Nassau
Four season mountain retreat with hot tub!
4 bedrooms, 5 beds, 2.5 bathrooms
21–26 Sept
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Cottage in New Lebanon
The Writer's Cottage
2 bedrooms, 2 beds, 1 bathroom
28 Oct – 2 Nov
4.94 out of 5 average rating, 216 reviews
Top guest favourite
Flat in New Lebanon
Loft Space above Brewery
1 bedroom, 3 beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Chalet in Averill Park
A Hidden Sparrow
4 bedrooms, 4 beds, 1.5 bathrooms
15–20 Sept
4.93 out of 5 average rating, 103 reviews
Flat in New Lebanon
Spring Hill Cottage 3rd Bedroom in New Lebanon
1 bedroom, 1 queen bed, 1 bathroom
1–6 Feb
Guest favourite
Home in Stephentown
Fam-Friendly Berkshire Views and Private Swim Pond
3 bedrooms, 4 beds, 1.5 bathrooms
15–20 Sept
4.89 out of 5 average rating, 36 reviews
Top guest favourite
Cabin in Stephentown
Stylish Mountain Cabin Close To Cherry Plain Park
3 bedrooms, 5 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 bathrooms
20–25 Sept
4.94 out of 5 average rating, 47 reviews