
Chalet holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham chalet rentals
Family-friendly chalet rentals

Daydream Mountain Art-Chateau | Hot Tub & Pool

Hunter Chalet 1 ml to Slopes Privately Convenient

Private Catskills Home w. Hot Tub, near Ski Mnt

*NEW GUT RENO 2023*4SeasonNirvana*HotTub*WiFi*

Secluded home by Hunter Mountain

2BDR- Cozy Windham/Hunter Escape

Cozy Silo Home w Mountain Views near Woodstock

Marigold - Stream side Cabin W/Hot Tub & Fireplace
Luxury chalet rentals

Blue Spruce Chalet — Hot Tub, Pet Friendly

Windham West Chalet

Modern Mountain Chalet on 15 Acre Catskills Estate

Enchanting Upstate Cabin w Pool, Firepit

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

Modern Chalet with Panoramic Views on 22 Acres

Secluded Woodstock Retreat with Pool and Sauna

Charming & Private Catskill Chalet
Lakefront chalet rentals

Lake &Hunter Ski Resort Luxury Chalet/HotTub/Sauna

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

Large & Sunny Lakefront Home-kayaks/fire pit/games

Waterfront Lake Home, close to Hunter & Windham

Eagles' retreat

Maple Lodge - Luxury Cabin

Lakefront Chalet|Hudson, Skiing | 90+ 5 star revs.
Destinations to explore
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- Belleayre Mountain Ski Center
- Windham Mountain
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Howe Caverns
- Albany Center Gallery
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Taconic State Park
- Glimmerglass State Park
- Walkway Over the Hudson State Historic Park
- Zoom Flume
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Opus 40
- Naumkeag
- Thaddeus Hait Farm
- Butternut Ski Area and Tubing Center
- Plattekill Mountain
- Huck Finn’s Playland, Albany
- Peebles Island State Park
- Pineridge Cross Country Ski Area
- Hancock Shaker Village