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Search results; Over 1,000 homes in Stephentown

Look out over the valley from this Stephentown chalet on 120 wooded acres
3 bedrooms, 4 beds, 1.5 private baths
Aug 14 – 19
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5.0 out of 5 average rating, 13 reviews
Guest favorite
This Stephentown apartment gives you a deck, fire pit, and hillside quiet
4.99 out of 5 average rating, 109 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 14 – 19
Guest favorite
This remodeled Stephentown apartment gives you a private arcade and soaking tub
4.96 out of 5 average rating, 50 reviews, 2 bedrooms, 4 beds, 1 bath
Aug 16 – 21
Top guest favorite
This Hancock guesthouse sits on a 40-acre llama farm you can explore
5.0 out of 5 average rating, 484 reviews, 1 bed, 1 bath
Sep 11 – 16
This Hancock ranch gives you 200 acres of walking trails and country views
New place to stay, 3 bedrooms, 4 beds, 1 bath
Aug 13 – 18
Guest favorite
This brand-new Stephentown studio puts you in a historic 1860s railroad hotel
4.83 out of 5 average rating, 30 reviews, 3 beds, 1 bath
Aug 16 – 21
Guest favorite
This Stephentown house gives you 38 secluded acres and a private swim pond
4.89 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 1.5 baths
Aug 23 – 28
Top guest favorite
Soak in sunsets from the porch of this Berkshires cabin with lake access
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 5 beds, 2 baths
Aug 18 – 23
This lodge-style Hancock retreat gives you a heated pool, hot tub, and game room
5.0 out of 5 average rating, 3 reviews, 13 bedrooms, 26 beds, 12.5 baths
Sep 7 – 12
Guest favorite
This remodeled Stephentown triplex gives you an arcade, fire pits, and mountain air
4.89 out of 5 average rating, 18 reviews, 5 bedrooms, 5 beds, 3 baths
Aug 16 – 21
Guest favorite
Look out over the mountains from this Stephentown house on 15 wooded acres
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 13 – 18
Superhost
This historic 1860s Stephentown hotel gives you four apartments and arcade rooms
5.0 out of 5 average rating, 4 reviews, 10 bedrooms, 10 beds, 6 baths
Aug 16 – 21
Top guest favorite
This wooded Stephentown home lets you take in sunsets from a private balcony
4.97 out of 5 average rating, 31 reviews, 1 bedroom, 1 bed, 1 bath
Oct 20 – 25
Guest favorite
Sip coffee in the English gardens at this treetop Canaan guesthouse on 3 acres
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 24 – 29
Top guest favorite
Look out over Burden Lake from the porch of this single-level Albany house
4.89 out of 5 average rating, 141 reviews, 3 bedrooms, 3 beds, 1 bath
Sep 8 – 13
Guest favorite
This bright, newly renovated Pittsfield apartment gives you a private backyard
4.92 out of 5 average rating, 324 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 23 – 28
Top guest favorite
A fully renovated 1771 sawmill in New Lebanon where you’ll find creek views and gardens
4.99 out of 5 average rating, 384 reviews, 1 bedroom, 2 beds, 2 baths
Sep 5 – 10
Guest favorite
This Hancock cottage sits you on 13 private acres with a fire pit and fireplace
4.89 out of 5 average rating, 208 reviews, 1 bedroom, 2 beds, 1 bath
Sep 1 – 6
Guest favorite
This rustic A-frame in Petersburgh gives you 300 acres of trails and a fire pit
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 2 beds, 1 bath
Aug 23 – 28