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Search results; Over 1,000 homes in Stephentown

Camper/RV in Stephentown
Your Glamping Getaway
1 bedroom, 2 beds, 1 private bath
Aug 30 – Sep 4
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4.91 out of 5 average rating, 11 reviews
Guest favorite
Apartment in Stephentown
Cozy 2-Bedroom Vacation Apartment
2 bedrooms, 3 beds, 1 bath
Sep 14 – 19
4.99 out of 5 average rating, 109 reviews
Guest favorite
Apartment in Stephentown
2 Bed Berkshire Getaway @ Stephentown Hotel
2 bedrooms, 4 beds, 1 bath
Aug 29 – Sep 3
4.96 out of 5 average rating, 50 reviews
Top guest favorite
Guesthouse in Stephentown
Dog Friendly Studio
1 queen bed, 1 bath
Sep 11 – 16
5.0 out of 5 average rating, 486 reviews
Home in Stephentown
Ioka Valley Farm's Little Farm House
3 bedrooms, 4 beds, 1 bath
Aug 23 – 28
New place to stay
Guest favorite
Apartment in Stephentown
Berkshires Apartment @ the Stephentown Hotel
3 beds, 1 bath
Sep 7 – 13
4.83 out of 5 average rating, 30 reviews
Guest favorite
Home in Stephentown
Fam-Friendly Berkshire Views and Private Swim Pond
3 bedrooms, 4 beds, 1.5 baths
Aug 23 – 28
4.89 out of 5 average rating, 36 reviews
Top guest favorite
Cabin in Stephentown
Stylish Mountain Cabin Close To Cherry Plain Park
3 bedrooms, 5 beds, 2 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 28 reviews
Home in Stephentown
13BR Retreat | Heated Pool, Hot Tub + Game Room
13 bedrooms, 26 beds, 12.5 baths
Sep 7 – 12
5.0 out of 5 average rating, 3 reviews
Guest favorite
Apartment in Stephentown
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
5 bedrooms, 5 beds, 3 baths
Aug 30 – Sep 4
4.89 out of 5 average rating, 18 reviews
Superhost
Home in Stephentown
The entire Stephentown Hotel! 28 person occupancy
10 bedrooms, 10 beds, 6 baths
Sep 7 – 13
5.0 out of 5 average rating, 4 reviews
Guest favorite
Home in New Lebanon
Unplug in the Berkshires | Your Summer Escape
3 bedrooms, 4 beds, 2 baths
Aug 23 – 28
4.91 out of 5 average rating, 69 reviews
Top guest favorite
Home in Lanesborough
Berkshires Home-Near Williams College
3 bedrooms, 3 beds, 2.5 baths
Aug 28 – Sep 2
5.0 out of 5 average rating, 30 reviews
Top guest favorite
Chalet in Averill Park
A Hidden Sparrow
4 bedrooms, 4 beds, 1.5 baths
Sep 8 – 13
4.94 out of 5 average rating, 101 reviews
Top guest favorite
Apartment in New Lebanon
Folk Art Studio: 1-bedroom near the Berkshires
1 bedroom, 2 beds, 1 bath
Sep 4 – 9
5.0 out of 5 average rating, 31 reviews
Guest favorite
Farm stay in New Lebanon
NEW RENO - Chalet-style farm loft near Tanglewood
1 bedroom, 3 beds, 1 bath
Aug 23 – 28
4.92 out of 5 average rating, 73 reviews
Guest favorite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 baths
Aug 30 – Sep 4
4.89 out of 5 average rating, 38 reviews
Top guest favorite
Vacation home in Stephentown
Quiet, peaceful wooded setting.
1 bedroom, 1 queen bed, 1 bath
Oct 20 – 25
4.97 out of 5 average rating, 31 reviews
Guest favorite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 14 reviews