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Vacation rentals in Berkshire County

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Top-rated holiday rentals in Berkshire County

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

Guest favourite
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
5 – 12 Sept
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.
24 Apr – 1 May
Guest favourite
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!
4 – 11 Apr

Popular amenities for Berkshire County holiday rentals

Other great holiday rentals in Berkshire County

Guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
14 – 21 Apr
Guest favourite
Guesthouse in Lenox
The Granary at House on Golden Hill
28 Apr – 5 May
Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
22 – 29 Oct
Guest favourite
Apartment in Great Barrington
Private En Suite in Beautiful Victorian
16 – 23 Nov
Guest favourite
Loft in Great Barrington
The Old Red Barn
11 – 18 Mar
Guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
17 – 24 Sept
Guest favourite
Place to stay in North Adams
Berkshire Mountain Top Chalet
23 – 30 May
Guest favourite
Guesthouse in Stephentown
Dog Friendly Studio
4 – 11 Jan
Guest favourite
Home in Lee
Cozy Berkshires Cottage
22 – 29 May
Guest favourite
Cottage in Becket
Cozy lakeside cottage
12 – 19 Nov
Guest favourite
Home in Dalton
The Yellow House
30 Sept – 7 Oct
Guest favourite
Apartment in Canaan
Mountain View Getaway
21 – 28 Dec

Destinations to explore