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Chalet vacation rentals in Berkshire County

Find and book unique chalets on Airbnb

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Top-rated chalet rentals in Berkshire County

Guests agree: these chalets 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 7 – 14
$352 per night
4.94 out of 5 average rating, 341 reviews
Guest favorite
Chalet in Great Barrington
Berkshire "ZEN" Chalet
"ZEN" Palace Chalet perfect spot to chill & relax after a day of exploring or skiing. SPACIOUS,secluded,quiet, great grounds -3 bdrm 2 ba with LUSH VIEWS endless windows. BEAUTIFUL exposed wood beams & ceilings throughout. Super family friendly. 5 min GREAT BARRINGTON, Butternut, Catamount, great food, nature trails, lakes, great shopping & farmer's markets. Close to STOCKBRIDGE,Tanglewood, Norman Rockwell Museum, Wheatleigh, Kirpalu,Canyon Ranch & HUDSON NY. Accessible knowledgable local host.
Jan 25 – Feb 1
$225 per night
4.96 out of 5 average rating, 52 reviews
Guest favorite
Chalet in Averill Park
A Hidden Sparrow
/\ Keeping it cozy, yet modern. Our take on hygge minimalism. A Hidden Sparrow is a classic mid-century A-frame nestled on 60+ acres for hiking and has a picturesque creek that flows in the front of the property. With fresh upgrades, tasteful aesthetic and comfy accommodations, A Hidden Sparrow is an idyllic sanctuary offering complete privacy for your next getaway. This all season escape is the perfect place to disconnect from your typical dwelling and enjoy everything nature has to offer. /\
Aug 17 – 24
$277 per night
4.93 out of 5 average rating, 45 reviews

Popular amenities for Berkshire County chalet rentals

Family-friendly chalet rentals

Guest favorite
Chalet in New Marlborough
Modern & Secluded on 40 Acres - Fast Wi-fi
Oct 11 – 18
$392 per night
4.92 out of 5 average rating, 50 reviews
Guest favorite
Chalet in Lee
Waterfront lakehouse in Berkshires
May 5 – 12
$400 per night
4.81 out of 5 average rating, 59 reviews
Guest favorite
Chalet in Richmond
Updated Berkshires Chalet Mins to Tanglewood/Lenox
Jan 22 – 29
$431 per night
4.98 out of 5 average rating, 86 reviews
Chalet in Stephentown
Ski Cottage in the Berkshire hills
Jun 21 – 28
$185 per night
4.93 out of 5 average rating, 14 reviews
Chalet in Monterey
Stunning Log Cabin
Aug 20 – 27
$629 per night
5.0 out of 5 average rating, 10 reviews
Chalet in Stockbridge
The Millhouse
Jan 7 – 14
$280 per night
4.6 out of 5 average rating, 5 reviews

Destinations to explore