Chalet vacation rentals in Windham
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Top-rated chalet rentals in Windham
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 Windham chalet rentals
Family-friendly chalet rentals
Chalet in Willow
4.88 out of 5 average rating, 138 reviewsCozy Silo with Sunset Views
Jun. 8 – 15
Chalet in Woodstock
4.94 out of 5 average rating, 116 reviewsMarigold - Stream side Cabin W/Hot Tub & Fireplace
Sep. 8 – 15
Chalet in Hunter
4.89 out of 5 average rating, 134 reviewsVintage 70s Ski Chalet- minutes from Ski slopes!
Sep. 14 – 21
Chalet in East Jewett
4.98 out of 5 average rating, 93 reviewsHunter Pines
May 26 – Jun. 2
Chalet in Fleischmanns
5.0 out of 5 average rating, 37 reviewsChalet with Breathtaking Views
Sep. 28 – Oct. 5
Chalet in Hensonville
4.97 out of 5 average rating, 321 reviews2BDR- Cozy Windham/Hunter Escape
May 30 – Jun. 6
Chalet in Margaretville
4.89 out of 5 average rating, 200 reviewsRunning Horse Cottage
Jun. 24 – Jul. 1
Chalet in Hunter
4.92 out of 5 average rating, 154 reviewsHunter Chalet 1 ml to Slopes Privately Convenient
Oct. 31 – Nov. 7
Luxury chalet rentals
Chalet in Mount Tremper
4.98 out of 5 average rating, 127 reviewsSecluded Woodstock Retreat with Pool and Sauna
Sep. 4 – 11
Chalet in Windham
4.96 out of 5 average rating, 84 reviewsLuxury Lodge with Slope Views - 5 Min to Skiing
May 13 – 20
Chalet in Windham
4.96 out of 5 average rating, 48 reviewsWindham - Hot Tub, Game Room, Fire Pit, Ski Views
Nov. 14 – 21
Chalet in Prattsville
4.99 out of 5 average rating, 96 reviewsLuxury Chalet with mountain views, hot tub, sauna
Sep. 15 – 22
Chalet in Windham
4.96 out of 5 average rating, 80 reviewsFernwood Chalet! Hiking, Sauna and Hot tub!
Oct. 20 – 27
Chalet in Windham
4.93 out of 5 average rating, 61 reviewsWindham Mountian Chalet with hot tub
Jul. 12 – 19
Chalet in Maplecrest
4.97 out of 5 average rating, 75 reviewsSecluded Catskills Designer Lodge - Windham/Hunter
Jul. 10 – 17
Chalet in Hensonville
5.0 out of 5 average rating, 52 reviewsHilltop Family Escape + hot tub, 4 min to slopes
Aug. 2 – 9
Lakefront chalet rentals
Chalet in Feura Bush
4.67 out of 5 average rating, 12 reviewsWaterfront Lodge - 3000 sqft Private Lake
Dec. 26 – Jan. 2
Chalet in Athens
5.0 out of 5 average rating, 30 reviewsLakefront w/Dock! Kayak | Pools | Firepit | Games
May 14 – 21
Chalet in Athens
4.93 out of 5 average rating, 84 reviewsLakefront Chalet near Hudson Kayaks | Pools | Fun
Nov. 19 – 26
Chalet in Athens
4.82 out of 5 average rating, 38 reviewsLarge & Sunny Lakefront Home-kayaks/fire pit/games
May 30 – Jun. 6
Chalet in Fleischmanns
5.0 out of 5 average rating, 3 reviewsLuxe Catskills Chalet
Aug. 16 – 23
Chalet in Hunter
4.91 out of 5 average rating, 64 reviewsHunter Chalet
Jun. 24 – Jul. 1
Chalet in Athens
4.89 out of 5 average rating, 91 reviewsWaterfront Lake Home, close to Hunter & Windham
Nov. 29 – Dec. 6
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