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Search results; Over 1,000 homes in Stephentown

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Top guest favourite
Cabin in Stephentown
Stylish Mountain Cabin Close To Cherry Plain Park
3 bedrooms, 5 beds, 2 private bathrooms
17–22 Sept
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5.0 out of 5 average rating, 28 reviews
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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
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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
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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
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Home in Stephentown
13BR Retreat | Heated Pool, Hot Tub + Game Room
13 bedrooms, 26 beds, 12.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 3 reviews
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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
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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
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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
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Guest favourite
Home in Stephentown
Lovely Secluded Berkshire MTN View 4BR Near Swim
4 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 22 reviews
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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
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Guest favourite
Home in Stephentown
Fam-Friendly Berkshire Views and Private Swim Pond
3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Sept
4.89 out of 5 average rating, 36 reviews
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Guest favourite
Home in Stephentown
Converted Barn w/pond on 120 Acres
5 bedrooms, 7 beds, 2.5 bathrooms
18–23 Sept
4.98 out of 5 average rating, 48 reviews
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Home in Stephentown
Secluded Upstate House, 7 Acres Near Jiminy Peak
3 bedrooms, 2 beds, 2.5 bathrooms
17–22 Oct
New place to stay
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Top guest favourite
Home in Hancock
Grand 6BR Home by Jiminy | Hike • Hot Tub • Games
6 bedrooms, 14 beds, 5.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 64 reviews
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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
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Top guest favourite
Cottage in Averill Park
Cozy cottage with pool, walking distance to lake
3 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.95 out of 5 average rating, 171 reviews
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Top guest favourite
Cabin in East Nassau
Fall Foliage Luxury Cabin & View Autumn Adventures
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 109 reviews
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Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 237 reviews
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Guest favourite
Home in Hancock
Lovely Home in the Berkshires
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
4.89 out of 5 average rating, 18 reviews