Chalet vacation rentals in Western Massachusetts
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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 Elka Park
4.91 out of 5 average rating, 544 reviewsSecluded home by Hunter Mountain
Chalet in Town of Rockingham
4.96 out of 5 average rating, 113 reviewsFantastic Mountain Views, Vermont
Chalet in Cold Spring
4.89 out of 5 average rating, 372 reviewsMountain View Retreat
Chalet in Willow
4.88 out of 5 average rating, 139 reviewsCozy Silo with Sunset Views
Chalet in Woodstock
4.94 out of 5 average rating, 116 reviewsMarigold - Stream side Cabin W/Hot Tub & Fireplace
Chalet in Dover
4.97 out of 5 average rating, 104 reviewsGrey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
Chalet in Jewett
4.97 out of 5 average rating, 167 reviewsPrivate Renovated Catskills Home w. Hot Tub
Chalet in Windham
4.97 out of 5 average rating, 115 reviewsBeautiful Windham Chalet 2 minutes to the Mountain
Luxury chalet rentals
Chalet in Mount Tremper
4.98 out of 5 average rating, 127 reviewsSecluded Woodstock Retreat with Pool and Sauna
Chalet in Copake
4.98 out of 5 average rating, 40 reviewsPrivate upstate home nestled in the Hudson Valley
Chalet in Dover
5.0 out of 5 average rating, 14 reviewsGreen Mt Chalet: Magical Summer Hideaway w/Hot Tub
Chalet in Mount Tremper
4.98 out of 5 average rating, 93 reviewsModern Mountain Chalet on 15 Acre Catskills Estate
Chalet in Winhall
4.98 out of 5 average rating, 54 reviewsMountain view chalet with hot tub & fire pit!
Chalet in Dover
4.97 out of 5 average rating, 70 reviewsModern Mountain Chalet: hot tub-firepit-brook
Chalet in Leeds
4.94 out of 5 average rating, 97 reviewsCatskill Chalet: Hot Tub, Fire Pit, Cozy, Private
Chalet in Wilmington
5.0 out of 5 average rating, 40 reviewsBeautiful Home on 22 Acres w/Ponds Near Mt. Snow
Lakefront chalet rentals
Chalet in Hunter
4.99 out of 5 average rating, 129 reviewsTHE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
Chalet in Winchester
4.87 out of 5 average rating, 63 reviewsChalet Sonsie: A Sweetwater Stay
Chalet in Londonderry
4.98 out of 5 average rating, 95 reviewsModern 3-bedroom A-frame in Londonderry, VT
Chalet in Antrim
5.0 out of 5 average rating, 43 reviewsDirect Waterfront A-Frame, Close to 3 Ski Areas!
Chalet in Lee
4.81 out of 5 average rating, 59 reviewsWaterfront lakehouse in Berkshires
Chalet in Hadley
5.0 out of 5 average rating, 20 reviewsGreat Sacandaga Lake Chalet
Chalet in Athens
4.89 out of 5 average rating, 91 reviewsWaterfront Lake Home, close to Hunter & Windham
Chalet in Woodstock
4.86 out of 5 average rating, 22 reviews"Nirvana": A Lakefront Retreat
Destinations to explore
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