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Search results; Over 1,000 homes in Stephentown

Guest favourite
Flat in Stephentown
2 Bed Berkshire Getaway @ Stephentown Hotel
2 bedrooms, 4 beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 50 reviews
Home in Stephentown
13BR Retreat | Heated Pool, Hot Tub + Game Room
13 bedrooms, 26 beds, 12.5 bathrooms
10–15 Jul
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
Berkshires Apartment @ the Stephentown Hotel
3 beds, 1 bathroom
16–21 Aug
4.83 out of 5 average rating, 29 reviews
Top guest favourite
Guest house in Stephentown
Dog Friendly Studio
1 queen bed, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 474 reviews
Guest favourite
Flat in Stephentown
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
5 bedrooms, 5 beds, 3 bathrooms
12–17 Jul
4.88 out of 5 average rating, 17 reviews
Home in Stephentown
Ioka Valley Farm's Little Farm House
3 bedrooms, 4 beds, 1 bathroom
9–14 Jul
New place to stay
Top guest favourite
Flat in New Lebanon
Folk Art Studio: 1-bedroom near the Berkshires
1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Holiday home in Stephentown
Quiet, peaceful wooded setting.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Flat in New Lebanon
Airy apartment at the old boarding house
2 bedrooms, 3 beds, 1 bathroom
28 Aug – 2 Sept
4.97 out of 5 average rating, 117 reviews
Guest favourite
Apartment in Hancock
THE SLOPE slope-view Country Inn 1BR w/heated pool
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in New Lebanon
Loft Space above Brewery
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Cottage in New Lebanon
The Writer's Cottage
2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
4.94 out of 5 average rating, 213 reviews
Guest favourite
Apartment in Hancock
SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
2 bedrooms, 6 beds, 2 bathrooms
18–23 Jul
4.96 out of 5 average rating, 57 reviews
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
4.94 out of 5 average rating, 35 reviews
Home in New Lebanon
Spring Hill Cottage in New Lebanon
2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Jul
New place to stay
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
Guest favourite
Home in New Lebanon
Unplug in the Berkshires | Your Summer Escape
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 65 reviews