Chalet vacation rentals in Western Massachusetts
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Western Massachusetts
Guests agree: these chalets are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Western Massachusetts chalet rentals
Family-friendly chalet rentals
Chalet in Catskill
4.96 out of 5 average rating, 184 reviewsDaydream Mountain Art-Chateau '73 | I ❤️ Catskill
Chalet in Jewett
4.97 out of 5 average rating, 173 reviewsPrivate Catskills Home w. Hot Tub, near Ski Mnt
Chalet in Ludlow
4.95 out of 5 average rating, 118 reviewsOkemo Ski Chalet with Hot Tub
Chalet in Elka Park
4.91 out of 5 average rating, 570 reviewsSecluded home by Hunter Mountain
Chalet in Hensonville
4.97 out of 5 average rating, 345 reviews2BDR- Cozy Windham/Hunter Escape
Chalet in Cragsmoor
5 out of 5 average rating, 237 reviewsScandinavian-Style Chalet with Scenic Views
Chalet in Willow
4.89 out of 5 average rating, 148 reviewsUnique Silo with Sunset Mountain Views
Chalet in Woodstock
4.94 out of 5 average rating, 117 reviewsMarigold - Stream side Cabin W/Hot Tub & Fireplace
Luxury chalet rentals
Chalet in Otis
4.9 out of 5 average rating, 52 reviewsThrill & Chill: Ski & Sauna in Winter Wonderland
Chalet in Copake
4.98 out of 5 average rating, 49 reviewsPrivate upstate home nestled in the Hudson Valley
Chalet in Windham
4.98 out of 5 average rating, 109 reviewsGorgeous Modern Lodge w/ Mt View - 5 Min to Skiing
Chalet in Wilmington
5 out of 5 average rating, 51 reviewsBeautiful Home on 22 Acres w/Ponds & Central A/C
Chalet in Maplecrest
4.97 out of 5 average rating, 77 reviewsSecluded Catskills Designer Lodge - Windham/Hunter
Chalet in Dover
5 out of 5 average rating, 36 reviewsNew! Custom Chalet minutes from Mt Snow w/ Hottub
Chalet in Winhall
4.88 out of 5 average rating, 68 reviewsSpacious Chalet W/ Endless Entertainment THE BARN
Chalet in Windham
5 out of 5 average rating, 10 reviewsDisco Chalet|Luxury|Sauna|HotTub|Firepit|Kidsroom
Lakefront chalet rentals
Chalet in Antrim
4.94 out of 5 average rating, 78 reviewsDirect Waterfront A-Frame, Close to 3 Ski Areas!
Chalet in Hunter
4.98 out of 5 average rating, 140 reviewsTHE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
Chalet in Lee
4.83 out of 5 average rating, 65 reviewsWaterfront lakehouse in Berkshires
Chalet in Athens
4.89 out of 5 average rating, 102 reviewsWaterfront Lake Home, close to Hunter & Windham
Chalet in Athens
4.84 out of 5 average rating, 44 reviewsLarge & Sunny Lakefront Home-kayaks/fire pit/games
Chalet in Winchester
4.81 out of 5 average rating, 94 reviewsChalet Sonsie: A Sweetwater Stay
Chalet in Sunapee
4.94 out of 5 average rating, 78 reviewsLake Sunapee Get Away
Chalet in Woodstock
4.88 out of 5 average rating, 25 reviews"Nirvana": A Lakefront Retreat
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