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Search results; Over 1,000 homes in Stephentown

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Top guest favourite
Guest house in Stephentown
Dog Friendly Studio
Studio, 1 bed, 1 private bathroom
11–16 Sept
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5.0 out of 5 average rating, 487 reviews
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Home in Stephentown
13BR Retreat | Heated Pool, Hot Tub + Game Room
13 bedrooms, 26 beds, 12.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Stephentown
2 Bed Berkshire Getaway @ Stephentown Hotel
2 bedrooms, 4 beds, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 50 reviews
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Flat in Stephentown
Cozy 2-Bedroom Vacation Apartment
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 110 reviews
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Guest favourite
Flat in Stephentown
Berkshires Apartment @ the Stephentown Hotel
3 beds, 1 bathroom
7–13 Sept
4.84 out of 5 average rating, 31 reviews
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Superhost
Home in Stephentown
The entire Stephentown Hotel! 28 person occupancy
10 bedrooms, 10 beds, 6 bathrooms
7–13 Sept
5.0 out of 5 average rating, 4 reviews
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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
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Home in Stephentown
Farm House with Free passes to Ioka Valley Farm
3 bedrooms, 4 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Stephentown
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
5 bedrooms, 5 beds, 3 bathrooms
7–13 Sept
4.89 out of 5 average rating, 18 reviews
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Top guest favourite
Cabin in Stephentown
Stylish Mountain Cabin Close To Cherry Plain Park
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 28 reviews
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Flat in New Lebanon
Spring Hill Cottage 3rd Bedroom in New Lebanon
1 bedroom, 1 queen bed, 1 bathroom
1–6 Feb
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Top guest favourite
Home in Hancock
Corey Road Condo | @ Jiminy Peak • Pool • Hot Tub
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 60 reviews
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Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 37 reviews
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Guest favourite
Home in Stephentown
Fam-Friendly Berkshire Views and Private Swim Pond
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.89 out of 5 average rating, 36 reviews
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Top guest favourite
Home in New Lebanon
Berkshire Mountain home views, pool, Queechy Lake
4 bedrooms, 9 beds, 4 bathrooms
1–6 Sept
4.99 out of 5 average rating, 71 reviews
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Guest favourite
Home in New Lebanon
The Spencer House 7 Bedroom Berkshire Inn
7 bedrooms, 9 beds, 7 bathrooms
1–6 Sept
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Home in Hancock
Family Lodge at Jiminy Peak - Pools & Adventure
4 bedrooms, 9 beds, 3 bathrooms
1–6 Sept
4.95 out of 5 average rating, 57 reviews
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Top guest favourite
Chalet in Averill Park
A Hidden Sparrow
4 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
4.93 out of 5 average rating, 102 reviews
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Top guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 bathrooms
1–6 Sept
4.94 out of 5 average rating, 47 reviews