Chalet vacation rentals in Windham

Beautiful Windham Ski/Summer House

A spacious 4 bedroom house located in Windham, NY just 5 minutes from the mountain. Built in 2012. Brand new comfy couches just purchased March 2021. Beautifully decorated with large wood doors, stone fireplace, and granite countertops. Wake up to view of the slopes from the large windows. Truly breathtaking views year round. Four bedrooms three with queen beds and 1 with a bunk beds (full size beds/twin trundle on the bottom). Plus a couch located in the loft area. The house sleeps 12. Full basement with television and couch with a ping pong table, a basketball game and a fooseball table. There are 3 full bathrooms along with one half. The main floor has a fire place along with tv and a full kitchen and dining area all with full views of Windham mountain. Come see the leaves turn and enjoy Great hiking, biking, golf and skiing when the snow comes. One mile from town and Windham Mountain. Pricing for a week goes from Friday to Friday. Renters must be at least 25 years old. Please no pets are allowed at the house, this is a strict policy no exceptions. No parties allowed Cleaning fee additional Christmas and New Years week have a 4 day min. and MLK and Presidents day week have a 3 day min.

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!

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!

Secluded Cabin in Catskills Park on 20 acres

It's a secluded cabin and we kept it small and pristine for a reason. We also just planted cherry trees and apple tree...We kept it pristine so one can feel nature. And we dont have internet or Tv there otherwize it would be like being in the city. Get a feel for what it is like to be in a cabin in the woods. There is a whole flourishing ecosystem there with family of rabits, foxes, humming birds, bees, butterflies and birds. We are planting a garden and flowers. A place for hiking lovers.

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 Chalet w/HOT TUB, Outdoor TV and POOL Table

Welcome to the beautiful Catskills! Our 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!!

Hunter Pines

Located in a secluded woodland, surrounded by state lands. This Chalet style house, is near Hunter & Windham Ski Mtns., and close to Colgate Lake. Enjoy a nice campfire or star gazing on 6 private acres our home is fully stocked to meet all your needs. New Keurig coffee machine for those coffee lovers. Cable TV & WIFI with a cosy fireplace, sledding on property, we have sleds, lots of games, ping pong/pool table, classic record collection and so much more, so far only 5 star reviews.

Unique BellEayre River retreat

#2024-STR-AO-85 As seen in Chronogram magazine Chronogram/docs/chronogram-april-2023 High ceilings, Rough cut beams, All new HVAC and Hearthstone soapstone wood burning stove. Ping pong table. With Back deck tranquil getaway, you see and hear only the water flow with wrap around 4 season river right off deck. Close to scenic hiking, skiing, river tubing, and great restaurants along "Rapid Water"- The Algonquin Nation word for "Shandaken". Dogs welcome (Up to 2), sorry no cat

Spacious cabin w/mountain views & woodstove

NOTE: Click “Show More” to read the full description. Home with stunning views perfectly situated between Roxbury and Stamford! Drink your morning coffee at the bar on the deck overlooking the mountains, curl up with a good book in the reading nook, or explore the farms, mountains, and countryside of the beautiful Western Catskills. Cabin is situated on five beautiful acres at the end of a private drive. Beautiful sunrises over the mountains, with wide-open stargazing after dark.

Luxurious Chalet w/ Amazing Views Near Windham Mtn

Ski at Windham Mountain Club and stay with us just 7 miles away at this modern 3-bedroom/4-bed/2-bath modern log chalet perched high along the northernmost edge of Mt. Pisgah offering panoramic views and 22 acres of seclusion completely surrounded by nature. Located close to hiking trails, rivers, lakes, reservoirs, breweries and wineries as well as Hunter (17 mi), Catskill (26 mi) and Hudson (30 mi), this is the ideal location from which to explore the best of the Catskills.

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.