
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.

Gorgeous Modern Lodge w/ Mt View - 5 Min to Skiing
Plan your all-seasons escape to this gorgeous new mid-century modern chalet with can't-beat direct views of Windham Mtn, less than a 5 minute drive away. Situated between state land and an active creek, enjoy this mountain getaway's hot tub, firepit, game room, open floor plan and other luxury amenities. Just 2.5 hours from NYC, and minutes away to skiing (<5 min to Windham Mtn, 15 min to Hunter Mtn, 40 min to Belleayre Mtn), hiking, biking, swimming, golfing, fishing, vineyards and restaurants!

Catskills mountain view chalet
Come and enjoy our Catskills mountain view chalet. Escape the chaos of the city for peace and serenity. In our home you'll find an open concept kitchen/dining and living room space, a huge deck, 2 bedrooms, a newly renovated bathroom and a loft work space. Take in the country skyline view with a glass of wine on the deck while listening to meditative sounds of the babbling brook. Don't forget to bring groceries as the best way to enjoy the chalet is with a home cooked meal with those you love

Catskills Aframe, Water View, Goat Sanctuary
This charming Aframe is tucked into the Catskill mountains, with spectacular seasonal views of the Rondout Reservoir. This house has a cozy feel with rustic charm and is the perfect getaway for those wishing to escape to nature. Outdoor enthusiasts will enjoy numerous local hiking trails and we're just 25 minutes from popular areas such as Mohonk Preserve, Sams Point, Minnewaska. A goat sanctuary, animal lovers can visit with our over 30 rescue goats, chickens, dogs and of course, local wildlife

Windham Immaculate Ski Chalet Secluded Fire Pit
Super immaculate, upscale, classic ski chalet nestled on 1 private wooded acre. Close to Windham Mountain, & a short scenic drive to Hunter mountain. Features 3 bedrooms & 2 full baths & comfortably sleeps 4 adults and 4 children. Den & 2 bedrooms downstairs, complete with down comforters. 1 bedroom with a queen size bed, 1 with 2 bunk beds, sleeps 4, & full bath downstairs. Master bedroom upstairs. It has cathedral ceilings, large windows, fireplace mountain views in fall & winter. NO PETS!

Location! Mid-century A-frame 12 min walk to lifts
A one minute drive to Hunter Mountain base lodge or a 12 minute walk! Situated on a quiet dead end street and only 1/4 mile from where the lifts are. There are no homes on the opposite side of the street creating an open view to the river valley. You can often hear the river running. It functions like a 2-family house because it has a lower unit in the basement. There are two bedrooms plus a loft area with a convertible couch. We have kept many of the original mid-century features intact.

Chalet w/ Amazing Views on 22 Acres Near Windham
A nature-lover's oasis, this 3-bedroom/4-bed/2-bath log-built chalet with contemporary furnishings is perched high along the northernmost edge of the Catskill Mountains offering unforgettable panoramic views from inside and out across 22+ secluded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Windam (7 mi), Hunter (16 mi), Catskill (26 mi) and Hudson (29 mi), this is the ideal location from which to explore the best the Catskills has to offer.

Modern Mountain Chalet on 15 Acre Catskills Estate
This secluded "Frank Lloyd Wright" inspired home can be your own private mountain retreat and perfect haven for an escape from the city. Designed like a luxurious treehouse, the multi layers of porches and decks makes one feel as if they are sleeping in the clouds. The home offers rest and relaxation with the therapeutic effects of nature right at your doorstep and as a breathtaking backdrop. You'll be inspired by the beauty and peacefulness that awaits you from every corner of the home!

Catskill Chalet - A Relaxing Mountain Retreat
Enjoy the scenic Catskill Mountains in this Bavarian-style chalet situated on half an acre with valley views. Composed of modern luxuries and comforts, The Alpine Chalet is the perfect getaway for anyone looking to explore the Catskills. Only 6 mins to Full Moon Resort, 10 mins to Belleayre Ski Mountain, and 15 mins to Phoenicia/30 mins to Woodstock, an abundance of hiking trails, ski resorts, and charming towns await you! Follow us on Insta! @Alpine.Chalet STR License #2022-STR-AO-005

Catskills Fall Escape: Sauna|Hot tub|Mountain View
Escape to Le Chalet, your private modern luxury retreat in the heart of the Catskills, just 2.5 hours north of NYC. Located near multiple ski resorts (Windham, Hunter, Bellaeyre), scenic hiking trails, and fishing streams, this stylish designer space features breathtaking Mountain views, Chef's kitchen, and beautifully curated Outdoor spaces, perfect for relaxation. Relax in the cedar barrel sauna with a panoramic window, stargaze in the hot tub, and roast marshmallows by the firepit.

Secluded Fernwood Chalet, Hot Tub, & Sauna House
Come immerse yourself in the beauty of the Catskills and enjoy the Fernwood chalet featuring mountain views and set upon 32 acres with private hiking trails, a hot tub, and a sauna house! Enjoy skiing in the winter (9 min. To Windham mtn., 18 to Hunter)hiking when it's warmer, fishing, swimming holes, lakes, you name it! Several wonderful dining options in the town of Windham, farmers markets & festivals, and other excursions a short drive away, or simply zen out at Fernwood!

Beautiful Windham Chalet 2 minutes to the Mountain
Beautiful Chalet close to Skiing, snowboarding, sledding, snowshoeing, mountain biking, hiking, golfing, wine tasting, Windham and Hunter Mountain festivals, great restaurants, and more. Relax on the beautiful deck while taking in the mountain views or cozy up to the fire pit. Enjoy a Gorgeous modern kitchen, fireplace and wood burning stove. Many amenities including washer, dryer, dishwasher, microwave, coffeemaker, BBQ, and paper products. Free WiFi. Sleeps 11. Pet friendly.

Original A-Frame/sauna/quiet oasis
This chalet A-Frame was the first of it's kind built by the original owners of Hunter Mountain Ski bowl! It is a mere 500 steps to the front steps of their legendary lodge. The Chalet is perfectly preserved and in a magnificent location to experience all that Hunter and it's iconic ski hill have to offer. At the end your days adventures come home to a blue stone fire pit and make smores under the Catskill stars! The infrared sauna will melt away any stress!
Popular amenities for Windham chalet rentals
Family-friendly chalet rentals

Blue Spruce Chalet — Hot Tub, Pet Friendly

Rustic Mountain view Cabin 5 mins to Ski Area!

Secluded Cabin in Catskills Park on 20 acres

Catskills Chalet w/ Hot Tub | Near Ski Resorts

Secluded Woodstock Retreat with Pool and Sauna

Serene & Bright: Minnewaska Mtn Views ~ Deck ~BBQ

Luxe Party Retreat: Ski|Hottub|Karaoke|Game| Movie

1920s Windham Farmhouse - HotTub, Sauna
Luxury chalet rentals

Daydream Mountain Art-Chateau | Hot Tub & Pool

Catskills 5BR • Near Windham/Hunter • Deck+Firepit

Spacious cabin w/grill, firepit & mountain views

Enchanting Upstate Cabin w Pool, Firepit

Spruced Moose Lodge w. Hot Tub & open Pool to oct

Thorne Hollow - Mountain Ski Getaway with HotTub

Disco&Chill Luxe Chalet|Views|Sauna|Firepit|HotTub

Charming & Private Catskill Chalet
Lakefront chalet rentals

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 w/Dock! Kayak | Pools | Firepit | Games

Lakefront Chalet-Spacious | Dock-Kayaks |Guest Fav
Quick stats about chalet rentals in Windham

Nightly prices starting at
Windham vacation rentals start at $395 CAD per night before taxes and fees

Verified guest reviews
Over 620 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Windham rentals

5 Average rating
Windham stays are highly rated by guests—averaging 5 out of 5!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Windham Mountain
- Resorts World Catskills
- John Boyd Thacher State Park
- Howe Caverns
- Glimmerglass State Park
- Bash Bish Falls State Park
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Norman Rockwell Museum
- Taconic State Park
- Plattekill Mountain
- Hunter Mountain Resort
- Opus 40
- Albany Center Gallery
- Peebles Island State Park
- Berkshire Botanical Garden
- Hancock Shaker Village
- Huck Finn’s Playland, Albany
- Butternut Ski Area and Tubing Center
- Pineridge Cross Country Ski Area