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.

Superhost

Cabin in Stephentown

4.84 out of 5 average rating, 232 reviews

Cabin 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

$228 per night
Guest favorite

Home in Canaan

5.0 out of 5 average rating, 132 reviews

Country 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

$135 per night
Guest favorite

Cottage in Lanesborough

4.93 out of 5 average rating, 220 reviews

Stone 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

$147 per night

Popular amenities for Stephentown vacation rentals

Other great vacation rentals in Stephentown

Guest favorite

Apartment in Stephentown

4.92 out of 5 average rating, 25 reviews

2 Bed Berkshire Getaway @ Stephentown Hotel

May 12 – 19

$130 per night
Guest favorite

Apartment in Stephentown

5.0 out of 5 average rating, 49 reviews

Cozy 2-Bedroom Vacation Apartment

May 8 – 15

$103 per night
Guest favorite

Vacation home in Stephentown

4.94 out of 5 average rating, 17 reviews

Quiet, peaceful wooded setting.

May 13 – 20

$85 per night
Guest favorite

Yurt in Stephentown

4.91 out of 5 average rating, 89 reviews

Off Grid Yurt Right By The Best of The Berkshires

Jun 7 – 14

$94 per night
Guest favorite

Apartment in Canaan

5.0 out of 5 average rating, 81 reviews

Mountain View Getaway

Nov 17 – 24

$91 per night
Guest favorite

Apartment in Lanesborough

4.86 out of 5 average rating, 93 reviews

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse

Apr 29 – May 6

$94 per night
Guest favorite

Condo in Hancock

4.9 out of 5 average rating, 51 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

Oct 22 – 29

$136 per night
Guest favorite

Camper/RV in East Nassau

5.0 out of 5 average rating, 14 reviews

The Hawk's Nest

Jul 31 – Aug 7

$85 per night
Guest favorite

Apartment in Pittsfield

4.92 out of 5 average rating, 24 reviews

Comfortable Pittsfield Loft

Feb 1 – 8

$65 per night
Guest favorite

Home in Adams

4.91 out of 5 average rating, 64 reviews

Mountain View Hideaway

Feb 11 – 18

$104 per night
Guest favorite

Farm stay in Stephentown

4.87 out of 5 average rating, 30 reviews

Private Historic Farmhouse- 5 mins to Jiminy Peak

Apr 24 – May 1

$404 per night
Guest favorite

Cottage in Malden Bridge

5.0 out of 5 average rating, 19 reviews

Cozy, charming cottage by the creek

Jun 5 – 12

$111 per night

Destinations to explore