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 Cold Spring
4.89 out of 5 average rating, 372 reviewsMountain View Retreat
Oct. 15 – 22
Chalet in Willow
4.88 out of 5 average rating, 139 reviewsCozy Silo with Sunset Views
Sep. 3 – 10
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
Jul. 21 – 28
Chalet in Windham
4.97 out of 5 average rating, 115 reviewsBeautiful Windham Chalet 2 minutes to the Mountain
Nov. 27 – Dec. 4
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. 30 – Oct. 7
Chalet in Monterey
4.97 out of 5 average rating, 73 reviewsCozy French Country chalet
Mar. 16 – 23
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 Dover
4.95 out of 5 average rating, 100 reviewsWine Moose Hot tub Fireplace Sauna 9min to Mt Snow
Nov. 23 – 30
Chalet in Hunter
4.96 out of 5 average rating, 217 reviewsAlpine Charm between Hunter and Windham
Jan. 15 – 22
Chalet in Copake
4.98 out of 5 average rating, 40 reviewsPrivate upstate home nestled in the Hudson Valley
Dec. 7 – 14
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 Leeds
4.94 out of 5 average rating, 97 reviewsCatskill Chalet: Hot Tub, Fire Pit, Cozy, Private
Aug. 23 – 30
Chalet in Prattsville
4.99 out of 5 average rating, 99 reviewsLuxury Chalet with mountain views, hot tub, sauna
Jun. 1 – 8
Chalet in Dover
4.97 out of 5 average rating, 70 reviewsModern Mountain Chalet: hot tub-firepit-brook
Feb. 3 – 10
Lakefront chalet rentals
Chalet in Hunter
4.99 out of 5 average rating, 129 reviewsTHE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
Oct. 15 – 22
Chalet in Feura Bush
4.67 out of 5 average rating, 12 reviewsWaterfront Lodge - 3000 sqft Private Lake
May 28 – Jun. 4
Chalet in Winchester
4.87 out of 5 average rating, 63 reviewsChalet Sonsie: A Sweetwater Stay
Apr. 29 – May 6
Chalet in Athens
5.0 out of 5 average rating, 30 reviewsLakefront w/Dock! Kayak | Pools | Firepit | Games
Dec. 18 – 25
Chalet in Athens
4.93 out of 5 average rating, 85 reviewsLakefront Chalet near Hudson Kayaks | Pools | Fun
Nov. 28 – Dec. 5
Chalet in Hunter
4.91 out of 5 average rating, 64 reviewsHunter Chalet
Oct. 23 – 30
Chalet in Athens
4.82 out of 5 average rating, 38 reviewsLarge & Sunny Lakefront Home-kayaks/fire pit/games
Oct. 4 – 11
Chalet in Lee
4.81 out of 5 average rating, 59 reviewsWaterfront lakehouse in Berkshires
Jun. 4 – 11
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