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, 139 reviewsCozy Silo with Sunset Views
Sep 1 – 8
Chalet in Woodstock
4.94 out of 5 average rating, 116 reviewsMarigold - Stream side Cabin W/Hot Tub & Fireplace
Dec 8 – 15
Chalet in Hunter
4.89 out of 5 average rating, 134 reviewsVintage 70s Ski Chalet- minutes from Ski slopes!
Sep 28 – Oct 5
Chalet in East Jewett
4.98 out of 5 average rating, 93 reviewsHunter Pines
Jun 4 – 11
Chalet in Fleischmanns
5.0 out of 5 average rating, 37 reviewsChalet with Breathtaking Views
Feb 27 – Mar 6
Chalet in Hensonville
4.97 out of 5 average rating, 321 reviews2BDR- Cozy Windham/Hunter Escape
Jul 23 – 30
Chalet in Margaretville
4.89 out of 5 average rating, 200 reviewsRunning Horse Cottage
Nov 1 – 8
Chalet in Hunter
4.92 out of 5 average rating, 154 reviewsHunter Chalet 1 ml to Slopes Privately Convenient
Nov 9 – 16
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 Windham
4.99 out of 5 average rating, 84 reviewsGorgeous Modern Lodge w/ Mt View - 5 Min to Skiing
Jun 24 – Jul 1
Chalet in Windham
4.96 out of 5 average rating, 49 reviewsWindham - Hot Tub, Game Room, Fire Pit, Ski Views
Mar 18 – 25
Chalet in Windham
4.96 out of 5 average rating, 80 reviewsFernwood Chalet! Hiking, Sauna and Hot tub!
Oct 28 – Nov 4
Chalet in Prattsville
4.99 out of 5 average rating, 98 reviewsLuxury Chalet with mountain views, hot tub, sauna
Jul 23 – 30
Chalet in Maplecrest
4.97 out of 5 average rating, 75 reviewsSecluded Catskills Designer Lodge - Windham/Hunter
Jun 12 – 19
Chalet in Windham
4.93 out of 5 average rating, 61 reviewsWindham Mountian Chalet with hot tub
Jul 6 – 13
Chalet in Mount Tremper
4.98 out of 5 average rating, 93 reviewsModern Mountain Chalet on 15 Acre Catskills Estate
Apr 21 – 28
Lakefront chalet rentals
Chalet in Feura Bush
4.67 out of 5 average rating, 12 reviewsWaterfront Lodge - 3000 sqft Private Lake
Jan 10 – 17
Chalet in Athens
5.0 out of 5 average rating, 30 reviewsLakefront w/Dock! Kayak | Pools | Firepit | Games
Nov 3 – 10
Chalet in Athens
4.93 out of 5 average rating, 85 reviewsLakefront Chalet near Hudson Kayaks | Pools | Fun
Nov 27 – Dec 4
Chalet in Athens
4.82 out of 5 average rating, 38 reviewsLarge & Sunny Lakefront Home-kayaks/fire pit/games
Oct 5 – 12
Chalet in Fleischmanns
5.0 out of 5 average rating, 3 reviewsRed Kill Mountain Chalet
Oct 24 – 31
Chalet in Athens
4.89 out of 5 average rating, 91 reviewsWaterfront Lake Home, close to Hunter & Windham
Oct 22 – 29
Chalet in Hunter
4.91 out of 5 average rating, 64 reviewsHunter Chalet
Oct 23 – 30
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