Chalet vacation rentals in Windham

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

**Summer Booking Now Open- Thru Sept 30!** Secluded log home nestled in 5 acres of Catskill mountain forest, with 4 bedrooms & 3.5 baths (incl. basement with built-in full size bunks). Enjoy a sunroom, screened porch, pool+hot tub, projection screen home theater & a treehouse that resembles a floating pirate ship 30 feet up in the trees. We're renovating the kitchen & master bed with new walls of windows in May - pics to come! Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Moon Mountain House Windham - Fits 13 on 7 Acres

Welcome to The Moon Mountain House (@moonmountainhouse)! Beautiful winter ski chalet! Secluded home on 7 acres w/ massive deck; borders beautiful creek & untouched state land; sleeps 13. Skiing, hiking, golf, leaf peeping, apple picking, and more! 5 min to Windham Mntn, golf courses, Windham Vineyard, and Windham Main Street with restaurants, shops, bars. 10 min to Escarpment Trail hikes; 20 min to Hunter Mntn, Kaaterskill Falls, North/South Lake. Enjoy all the Catskills has to offer!

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.

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

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 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.

Windham Immaculate Ski Chalet w / Awesome Fire Pit

Ultra Clean, Modern Chalet, Close to Windham Mountain, & a short scenic drive to Hunter mountain: An upscale, classic ski chalet: 4 bdrms and 2 full baths. Sleeps 8 Den & 3 bedrooms downstairs, complete with down comforters. 1 bedroom with a full size bed, 1 with 2 twin beds, 1 with 2 bunk beds & a full bath downstairs. Master bedroom is upstairs, with alcove area that would be great for a crib. Cathedral ceilings, large windows with mountain views fall & winter. NO PETS ALLOWED

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.

Catskill Chalet: Hunter Mtn Oct Fest Hideaway

Camp Van Winkle is a place to relax, unwind & reclaim your sense of calm. 🌳 Escape to our cozy Catskills chalet, the perfect base for your iconic mountain getaway! 🏡 Relax and unwind in our charming home, featuring a spacious deck with a bubbling hot tub, perfect for stargazing after a day of adventure. 💫 We are lucky to be surrounded by some of the most spectacular hiking trials and waterfalls in the Catskills, we dare you not to fall in love! 😻