Chalet vacation rentals in The Berkshires
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Top-rated chalet rentals in The Berkshires
Guests agree: these chalets are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for The Berkshires chalet rentals
Family-friendly chalet rentals
Chalet in Elka Park
4.91 out of 5 average rating, 545 reviewsSecluded home by Hunter Mountain
Chalet in Willow
4.88 out of 5 average rating, 139 reviewsCozy Silo with Sunset Views
Chalet in Cold Spring
4.89 out of 5 average rating, 373 reviewsMountain View Retreat
Chalet in Town of Rockingham
4.96 out of 5 average rating, 114 reviewsFantastic Mountain Views, Vermont
Chalet in Woodstock
4.94 out of 5 average rating, 117 reviewsMarigold - Stream side Cabin W/Hot Tub & Fireplace
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
Chalet in Dover
4.97 out of 5 average rating, 104 reviewsGrey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
Luxury chalet rentals
Chalet in Hunter
4.96 out of 5 average rating, 217 reviewsAlpine Charm between Hunter and Windham
Chalet in Copake
4.98 out of 5 average rating, 40 reviewsPrivate upstate home nestled in the Hudson Valley
Chalet in Mount Tremper
4.98 out of 5 average rating, 93 reviewsModern Mountain Chalet on 15 Acre Catskills Estate
Chalet in Leeds
4.94 out of 5 average rating, 98 reviewsCatskill Chalet: Hot Tub, Fire Pit, Cozy, Private
Chalet in Warwick
5.0 out of 5 average rating, 47 reviewsMountain view retreat w/ hot tub, theater, and gym
Chalet in Dover
4.97 out of 5 average rating, 72 reviewsModern Mountain Chalet: hot tub-firepit-brook
Chalet in Dover
5.0 out of 5 average rating, 14 reviewsGreen Mt Chalet: Magical Summer Hideaway w/Hot Tub
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, 130 reviewsTHE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
Chalet in Winchester
4.88 out of 5 average rating, 65 reviewsChalet Sonsie: A Sweetwater Stay
Chalet in Carmel Hamlet
4.95 out of 5 average rating, 22 reviewsSecluded Lakefront Chalet 1hr to NYC. Dog friendly
Chalet in Londonderry
4.98 out of 5 average rating, 96 reviewsModern 3-bedroom A-frame in Londonderry, VT
Chalet in Athens
5.0 out of 5 average rating, 30 reviewsLakefront w/Dock! Kayak | Pools | Firepit | Games
Chalet in Lee
4.81 out of 5 average rating, 59 reviewsWaterfront lakehouse in Berkshires
Chalet in Athens
4.82 out of 5 average rating, 38 reviewsLarge & Sunny Lakefront Home-kayaks/fire pit/games
Chalet in Athens
4.89 out of 5 average rating, 91 reviewsWaterfront Lake Home, close to Hunter & Windham
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