Chalet vacation rentals in Berkshire County
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Berkshire County
Guests agree: these chalets are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Berkshire County chalet rentals
Family-friendly chalet rentals
Guest favorite
Chalet in Richmond
4.97 out of 5 average rating, 93 reviewsUpdated Berkshires Chalet Mins to Tanglewood/Lenox
Guest favorite
Chalet in Peru
4.92 out of 5 average rating, 270 reviewsSwiss Chalet Style Timberframe Home in Berkshires
Guest favorite
Chalet in New Marlborough
4.92 out of 5 average rating, 53 reviewsModern Secluded Ski Chalet | 40 Acres | Family
Chalet in Lee
4.83 out of 5 average rating, 65 reviewsWaterfront lakehouse in Berkshires
Chalet in Monterey
5 out of 5 average rating, 10 reviewsStunning Log Cabin with brand new Pickleball court
Chalet in Stephentown
5 out of 5 average rating, 13 reviewsSki Cottage in the Berkshire hills
Guest favorite
Chalet in Otis
4.95 out of 5 average rating, 382 reviewsMid-Century Glass Octagon in the Berkshires
Guest favorite
Chalet in Monterey
4.98 out of 5 average rating, 80 reviewsCozy French Country chalet
Luxury chalet rentals
Guest favorite
Chalet in Otis
4.9 out of 5 average rating, 52 reviewsThrill & Chill: Ski & Sauna in Winter Wonderland
Guest favorite
Chalet in New Marlborough
4.92 out of 5 average rating, 53 reviewsModern Secluded Ski Chalet | 40 Acres | Family
Chalet in Monterey
New place to stayLake/Ski House Getaway
Chalet in Monterey
5 out of 5 average rating, 10 reviewsStunning Log Cabin with brand new Pickleball court
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