Chalet vacation rentals in Massachusetts
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Massachusetts
Guests agree: these chalets are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Massachusetts 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
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
5 out of 5 average rating, 10 reviewsStunning Log Cabin with brand new Pickleball court
Chalet in Monterey
New place to stayLake/Ski House Getaway
Destinations to explore
- Chalet rentals United States
- Pet-friendly rentals Massachusetts
- Rentals with a sauna Massachusetts
- Fitness-friendly rentals Massachusetts
- Barn rentals Massachusetts
- Rentals with breakfast Massachusetts
- Rentals with a patio Massachusetts
- Cottage rentals Massachusetts
- Rentals with a washer and dryer Massachusetts
- Serviced apartment rentals Massachusetts
- Apartment rentals Massachusetts
- Guesthouse rentals Massachusetts
- Bungalow rentals Massachusetts
- Beach house rentals Massachusetts
- Ski-in/ski-out rentals Massachusetts
- Resort rentals Massachusetts
- Rentals with a hot tub Massachusetts
- Rentals with an accessible height bed Massachusetts
- Loft rentals Massachusetts
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- Family-friendly rentals Massachusetts
- Cabin rentals Massachusetts
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- Hotel rentals Massachusetts
- Rentals with pools Massachusetts
- Rentals with an accessible height toilet Massachusetts
- Kid-friendly rentals Massachusetts
- Tiny house rentals Massachusetts
- Lakehouse rentals Massachusetts
- Rentals with beach access Massachusetts
- Rentals with an EV charger Massachusetts
- Rentals with a fire pit Massachusetts
- Condo rentals Massachusetts
- Rentals with a home theater Massachusetts
- Bed and breakfasts Massachusetts
- Waterfront rentals Massachusetts
- House rentals Massachusetts
- Villa rentals Massachusetts
- Rentals with outdoor seating Massachusetts
- Private suite rentals Massachusetts
- Rentals with a kayak Massachusetts
- Rentals with a fireplace Massachusetts
- Mansion rentals Massachusetts
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- Monthly Rentals Massachusetts
- 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
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- Mansion Rentals United States
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- Holiday Bungalows United Kingdom
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- Holiday Apartments Australia
- Holiday Houses United States
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- 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
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- Things to do Massachusetts
- Food and drink Massachusetts
- Nature and outdoors Massachusetts
- Sightseeing Massachusetts
- Art and culture Massachusetts