Chalet vacation rentals in Windham

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Windham

Guests agree: these chalets are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Chalet in Fleischmanns

4.91 out of 5 average rating, 115 reviews

Berushka Cottage: 9 min to Belleayre, Views, WFH

Cozy 2 bedroom cabin with beautiful mountain views and strong work from home WIFI! 2 hrs from NYC and 9 min to Belleayre skiing (and lake swimming in summer) and Spillian venue. We love this wooded property which is private but not desolate. At the top of a hill up a distance from a quiet road we have great views of the mountains. We love seeing wildlife on the property including turkeys, deer, bunnies, chipmunks, hawks, and lots of birds. A relaxing getaway from it all! @berushka_cottage on IG

Superhost

Chalet in Gilboa

4.88 out of 5 average rating, 101 reviews

Modern Chalet w/Outdoor TV & Covered HOT TUB+Trail

Welcome to the beautiful Catskills! Our new beautiful A-Frame Chalet is situated on 6 acres of private forested land with lovely views of nature. Come stay in the fresh air! The chalet is fully stocked to be enjoyed for all seasons! Relax under the covered patio in all weather (rain or snow) in the HOT TUB or lounging on outdoor sectional while watching some NETFLIX/YOUTUBE TV all year round on our OUTDOOR TV, shoot a game of POOL in our upstairs Loft, or take a hike through our private TRAIL!!

Guest favorite

Chalet in Prattsville

4.99 out of 5 average rating, 113 reviews

Sauna|Hot tub|Hunter Mountain View|Chef's kitchen

Escape to Le Chalet, your private modern luxury retreat in the heart of the Catskills, just 2.5 hours north of NYC. Located near scenic hiking trails, fishing streams, and ski resorts (Windham, Hunter), 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. Plan your getaway today!

Guest favorite

Chalet in Tannersville

5 out of 5 average rating, 174 reviews

Catskill Chalet: Romantic Fall Escape w/Hot Tub

Camp Van Winkle is a place to relax, unwind & reclaim your sense of calm. Take time to connect with family and friends and discover the magic of the Legendary Catskills. In the summer, there's hiking, biking, boating & swimming. Winter brings skiing at Hunter & Windham, ice skating & cozy evenings by a warm fire. Take a soak in the Spa! Enjoy the quiet, the starry night sky & the fresh air all year round. Designed with love and care, we invite you to relax and stay awhile! Almost Home!!

Guest favorite

Chalet in Leeds

4.95 out of 5 average rating, 112 reviews

Catskill Chalet: Hot Tub, Fire Pit, Cozy, Private

**Steep driveway-highly suggest SUV** Step into the comfort of this stylish 3BR, 2.5 bath chalet, 2 hours from NYC. Nestled in tranquility, offering a perfect escape from the everyday hustle and bustle. It promises a secluded retreat with a rich amenity list, immersed in the dreamy natural ambiance, close to the town of Catskill, NY. ✔ 3 Comfy BRs ✔ Fully Equipped Kitchen ✔ Pool Table ✔ Front Deck (Electric BBQ) ✔ Hot Tub ✔ Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Parking See more below!

Guest favorite

Chalet in Big Indian

4.95 out of 5 average rating, 132 reviews

The Alpine Chalet - A Cozy, Catskill Mountain Home

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

Guest favorite

Chalet in Windham

4.97 out of 5 average rating, 105 reviews

Luxury Lodge with Slope Views - 5 Min to Skiing

Plan your all-seasons escape to this beautiful, luxury chalet with direct views of Windham Mt., just a 5 minute drive to the slopes. Situated at the end of a private road on 3+ acres, enjoy this mountain getaway's hot tub, oversized deck, pond, firepit, huge game room, and other modern 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!

Guest favorite

Chalet in Windham

4.96 out of 5 average rating, 119 reviews

Beautiful Windham Chalet 2 minutes to the Mountain

Beautiful Chalet close to Skiing, snowboarding, sledding, snowshoeing, mountain biking, hiking, golfing, wine tasting, zip lining, 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. All amenities including washer, dryer, dishwasher, microwave, coffeemaker, BBQ, and paper products. Free WiFi. Sleeps 11. Pet friendly.

Guest favorite

Chalet in Maplecrest

4.97 out of 5 average rating, 235 reviews

Windham Chalet w BBQ Hut, Pizza Oven and Hot tub

Escape to a peaceful retreat just five minutes from Windham! Our private cabin offers relaxation and comfort, featuring a spacious deck with a hot tub, swing bed, gas grill, and bar seating. Enjoy the unique charm of our Scandinavian BBQ hut, perfect for year-round grilling and cozy gatherings. Whether rain or shine, you can soak in the beauty of nature, grill, or gather around the fire pit under the covered deck. Offering an escape for nature lovers seeking tranquility and comfort!

Guest favorite

Chalet in Tannersville

4.92 out of 5 average rating, 235 reviews

Romantic Chalet~ Hot Tub ~ Near Hunter Mountain

The Catskills Hideaway is a place to step back in time, unwind with a cocktail by the fire, soak in the hot tub, read a book in one of the hanging chairs, toast marshmallows with friends, prepare a special meal in the kitchen, ski your heart out, hike one of the many local trails, visit the falls, enjoy the local restaurants- whatever you’re dreaming about for your Catskill escape- this is THE PLACE! Hunter Mountain 4.8 miles Windham Mountain 12.6 miles Kaaterskill Falls 4 miles

Guest favorite

Chalet in Hurley

4.98 out of 5 average rating, 210 reviews

Exquisite Chalet near to Woodstock's best scenery

Newly renovated 3 bedrooms, 2 baths chalet for 6, one mile from stunning Ashokan reservoir view, on private lane but in the heart of Catskills, 10 min from Woodstock, Kingston and exit 19 off hwy 87, with fireplace, wraparound deck, deer-proof yard, firepit, barbecue, veggie garden. Ideal for couples, families, friends. Minutes to ski, ice climbing, iceskating, swimming, hiking, rock climbing, tubing, fishing, scenic walks, biking trails, food markets & excellent restaurants.

Guest favorite

Chalet in Fleischmanns

4.88 out of 5 average rating, 208 reviews

Gorgeous Ski Chalet - 7 mi to Belleayre (hot tub)

This fully renovated chalet is close to Margaretville and Phoenicia. 7 mi to Belleayre. Close to hiking/biking. Secluded property with gorgeous pond and mountain views. 6 person hot tub! Great for couples/skiers/hikers/family/friends getaways. No smokers/cats. Extra charges: - $25 firewood/fire starters. - $50 pet fee per dog + $300 refundable deposit - $25 per guest > 5 guests. Booking constitutes agreeing to the liability waiver in the house manual for hot tub.