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.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
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
Destinations to explore
- Chalet rentals United States
- Chalet rentals New York
- Chalet rentals Massachusetts
- Chalet rentals Massachusetts
- Rentals with breakfast Berkshire County
- Condo rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Rentals with a patio Berkshire County
- Hotel rentals Berkshire County
- Rentals with beach access Berkshire County
- Beachfront rentals Berkshire County
- Monthly Rentals Berkshire County
- Kid-friendly rentals Berkshire County
- Rentals with a kayak Berkshire County
- Private suite rentals Berkshire County
- Rentals with pools Berkshire County
- House rentals Berkshire County
- Pet-friendly rentals Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Apartment rentals Berkshire County
- Rentals with lake access Berkshire County
- Bed and breakfasts Berkshire County
- Boutique hotel rentals Berkshire County
- Rentals with a fire pit Berkshire County
- Rentals with a fireplace Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a washer and dryer Berkshire County
- Farmstay rentals Berkshire County
- Fitness-friendly rentals Berkshire County
- Cottage rentals Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Rentals with an EV charger Berkshire County
- Guesthouse rentals Berkshire County
- Rentals with a sauna Berkshire County
- Waterfront rentals Berkshire County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do United States
- Food and drink United States
- Wellness United States
- Sports activities United States
- Nature and outdoors United States
- Entertainment United States
- Sightseeing United States
- Art and culture United States
- Things to do Massachusetts
- Art and culture Massachusetts
- Food and drink Massachusetts
- Sightseeing Massachusetts
- Nature and outdoors Massachusetts
- Things to do Berkshire County