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, 544 reviewsSecluded home by Hunter Mountain
May 8 – 15
Chalet in Cold Spring
4.89 out of 5 average rating, 371 reviewsMountain View Retreat
Oct 15 – 22
Chalet in Willow
4.88 out of 5 average rating, 139 reviewsCozy Silo with Sunset Views
Aug 27 – Sep 3
Chalet in Woodstock
4.94 out of 5 average rating, 116 reviewsMarigold - Stream side Cabin W/Hot Tub & Fireplace
Dec 4 – 11
Chalet in Jewett
4.97 out of 5 average rating, 167 reviewsPrivate Renovated Catskills Home w. Hot Tub
May 16 – 23
Chalet in Windham
4.97 out of 5 average rating, 115 reviewsBeautiful Windham Chalet 2 minutes to the Mountain
Nov 26 – Dec 3
Chalet in Dover
4.97 out of 5 average rating, 104 reviewsGrey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
Nov 11 – 18
Chalet in Hunter
4.89 out of 5 average rating, 134 reviewsVintage 70s Ski Chalet- minutes from Ski slopes!
Sep 28 – Oct 5
Luxury chalet rentals
Chalet in Mount Tremper
4.98 out of 5 average rating, 127 reviewsSecluded Woodstock Retreat with Pool and Sauna
Jul 22 – 29
Chalet in Hunter
4.96 out of 5 average rating, 217 reviewsAlpine Charm between Hunter and Windham
Jan 14 – 21
Chalet in Copake
4.98 out of 5 average rating, 40 reviewsPrivate upstate home nestled in the Hudson Valley
Dec 5 – 12
Chalet in Leeds
4.94 out of 5 average rating, 97 reviewsCatskill Chalet: Hot Tub, Fire Pit, Cozy, Private
Aug 24 – 31
Chalet in Mount Tremper
4.98 out of 5 average rating, 93 reviewsModern Mountain Chalet on 15 Acre Catskills Estate
Apr 22 – 29
Chalet in Prattsville
4.99 out of 5 average rating, 99 reviewsLuxury Chalet with mountain views, hot tub, sauna
Jul 23 – 30
Chalet in Dover
4.97 out of 5 average rating, 70 reviewsModern Mountain Chalet: hot tub-firepit-brook
Mar 31 – Apr 7
Chalet in Windham
4.96 out of 5 average rating, 49 reviewsWindham - Hot Tub, Game Room, Fire Pit, Ski Views
Mar 18 – 25
Lakefront chalet rentals
Chalet in Hunter
4.99 out of 5 average rating, 129 reviewsTHE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
Aug 21 – 28
Chalet in Winchester
4.87 out of 5 average rating, 62 reviewsChalet Sonsie: A Sweetwater Stay
Apr 22 – 29
Chalet in Athens
5.0 out of 5 average rating, 30 reviewsLakefront w/Dock! Kayak | Pools | Firepit | Games
Sep 5 – 12
Chalet in Feura Bush
4.67 out of 5 average rating, 12 reviewsWaterfront Lodge - 3000 sqft Private Lake
May 13 – 20
Chalet in Lee
4.81 out of 5 average rating, 59 reviewsWaterfront lakehouse in Berkshires
Jun 4 – 11
Chalet in Athens
4.89 out of 5 average rating, 91 reviewsWaterfront Lake Home, close to Hunter & Windham
Oct 22 – 29
Chalet in Athens
4.82 out of 5 average rating, 38 reviewsLarge & Sunny Lakefront Home-kayaks/fire pit/games
Oct 5 – 12
Chalet in Hunter
4.91 out of 5 average rating, 64 reviewsHunter Chalet
Oct 23 – 30
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