Vacation rentals in Stephentown
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Top-rated vacation rentals in Stephentown
Guests agree: these stays are highly rated for location, cleanliness, and more.
Cabin in Stephentown
4.84 out of 5 average rating, 232 reviewsCabin in the woods w cedar Hot Tub + private pond
The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.
Apr 20 – 27
Home in Canaan
5.0 out of 5 average rating, 132 reviewsCountry Cottage
Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.
Mar 12 – 19
Cottage in Lanesborough
4.93 out of 5 average rating, 220 reviewsStone School Cottage
Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.
Apr 14 – 21
Vacation rentals for every style
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Popular amenities for Stephentown vacation rentals
Other great vacation rentals in Stephentown
Apartment in Stephentown
4.92 out of 5 average rating, 25 reviews2 Bed Berkshire Getaway @ Stephentown Hotel
May 12 – 19
Apartment in Stephentown
5.0 out of 5 average rating, 49 reviewsCozy 2-Bedroom Vacation Apartment
May 8 – 15
Vacation home in Stephentown
4.94 out of 5 average rating, 17 reviewsQuiet, peaceful wooded setting.
May 13 – 20
Yurt in Stephentown
4.91 out of 5 average rating, 89 reviewsOff Grid Yurt Right By The Best of The Berkshires
Jun 7 – 14
Apartment in Canaan
5.0 out of 5 average rating, 81 reviewsMountain View Getaway
Nov 17 – 24
Apartment in Lanesborough
4.86 out of 5 average rating, 93 reviewsCozy Rustic Apt. in 18th c. Berkshire Farmhouse
Apr 29 – May 6
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Oct 22 – 29
Camper/RV in East Nassau
5.0 out of 5 average rating, 14 reviewsThe Hawk's Nest
Jul 31 – Aug 7
Apartment in Pittsfield
4.92 out of 5 average rating, 24 reviewsComfortable Pittsfield Loft
Feb 1 – 8
Home in Adams
4.91 out of 5 average rating, 64 reviewsMountain View Hideaway
Feb 11 – 18
Farm stay in Stephentown
4.87 out of 5 average rating, 30 reviewsPrivate Historic Farmhouse- 5 mins to Jiminy Peak
Apr 24 – May 1
Cottage in Malden Bridge
5.0 out of 5 average rating, 19 reviewsCozy, charming cottage by the creek
Jun 5 – 12
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