Vacation rentals in Berkshire County

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Top-rated vacation rentals in Berkshire County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Chalet in Otis

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Sep 26 – Oct 3

$352 per night$2,951 total

Cabin in Stephentown

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 24 – May 1

$228 per night$1,977 total
Guest favorite

Apartment in Copake Falls

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Jun 16 – 23

$95 per night$839 total

Popular amenities for Berkshire County vacation rentals

Other great vacation rentals in Berkshire County

Guest favorite

Cottage in Great Barrington

Cottage on Scenic Road

Nov 1 – 8

$117 per night$1,072 total
Guest favorite

Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

May 1 – 8

$267 per night$2,278 total
Guest favorite

Place to stay in North Adams

Berkshire Mountain Top Chalet

Apr 2 – 9

$342 per night$2,985 total
Guest favorite

Apartment in Great Barrington

Private En Suite in Beautiful Victorian

Jan 20 – 27

$96 per night$799 total
Guest favorite

Vacation home in Great Barrington

Home in Great Barrington. Steps from downtown!

Sep 18 – 25

$245 per night$2,034 total
Guest favorite

Home in Monterey

Charming cottage w/ gorgeous views.

Dec 26 – Jan 2

$145 per night$1,263 total
Guest favorite

Loft in Great Barrington

The Old Red Barn

May 2 – 9

$140 per night$1,229 total
Guest favorite

Home in Lee

Cozy Berkshires Cottage

May 27 – Jun 3

$111 per night$997 total
Guest favorite

Guesthouse in Stephentown

Dog Friendly Studio

Jan 9 – 16

$167 per night$1,392 total
Guest favorite

Apartment in Canaan

Mountain View Getaway

May 29 – Jun 5

$87 per night$774 total
Guest favorite

Guest suite in Great Barrington

Sweet 1-bedroom in the beautiful Berkshires

Mar 12 – 19

$82 per night$742 total
Guest favorite

Farm stay in Pittsfield

Private 2nd-floor studio on a working produce farm

Apr 16 – 23

$94 per night$775 total

Destinations to explore