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Search results; Over 1,000 homes in Stephentown

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Chalet in Stephentown
Ski Cottage in the Berkshire hills
3 bedrooms, 4 beds, 1.5 private bathrooms
22–27 Sept
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5.0 out of 5 average rating, 13 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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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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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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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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Home in Stephentown
13BR Retreat | Heated Pool, Hot Tub + Game Room
13 bedrooms, 26 beds, 12.5 bathrooms
12–17 Oct
4.75 out of 5 average rating, 4 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
21–26 Sept
4.89 out of 5 average rating, 36 reviews
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Home in Stephentown
Ioka's Little Farm House
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 4 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 Oct
5.0 out of 5 average rating, 28 reviews
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Guest favourite
Home in Stephentown
Converted Barn w/pond on 120 Acres
5 bedrooms, 7 beds, 2.5 bathrooms
23–28 Sept
4.98 out of 5 average rating, 48 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
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, 65 reviews
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Top guest favourite
Home in Stephentown
Berkshire Cabin
1 bedroom, 1 bed, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Home in Hancock
Lovely Home in the Berkshires
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.89 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Lanesborough
Berkshire Mountain House
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 43 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
27 Sept – 2 Oct
4.97 out of 5 average rating, 109 reviews
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Top guest favourite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 26 reviews