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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.

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Guest favourite
The spacious living area features high vaulted wooden ceilings and large windows that allow natural light to fill the room. Comfortable seating arrangements are available, including burgundy armchairs and a plaid sofa, creating a warm atmosphere for gatherings.
Chalet in Prattsville
4.93 out of 5 average rating, 100 reviews

Gorgeous Chalet with Mountain Views near Major Ski Resorts

Wake up to spectacular views and fresh mountain air in this classic chalet. The expansive living area features high, vaulted ceilings and outdoor spaces for relaxing conversations. If you are a nature lover or like to hunt, This is the place to be. You will find two bedrooms on the main floor, one with a queen bed and the other with two single beds. Additional guests have access to either the couch in the living room or a cozy loft area above. Everything is conveniently located on the main floor, with a nice sized kitchen/dining area. The house is in a residential area on a beautiful 30 acres. The hosts are available at anytime, and can be there in just a few minutes if needed. We welcome all communication and always prefer to greet our guests upon arrival, as well as seeing you off after your stay. The house is in a nice quiet residential area and just 20 minutes from Windham/Hunter Ski resorts. The resorts offer year-round activities ensuring groups of families or friends can have an excellent trip. The guest can park their cars in the house driveway. A relaxing evening is made easy in this large living area with ample seating for all. So gather your family and friends on your down time, pop some popcorn, turn on the TV and put your feet up in this cozy home away from home. After a long day you will have a restful nights sleep with accommodations for up to 6 guests. Two nice size private bedrooms available, one with a queen bed and the other with two single beds. A comfy second floor loft area will accommodate one guest, and the sofa in the main living area can also be used for one guest. Locally here in Prattsville you can pick up something from the supermarket and take advantage of access to a full kitchen back at the house or get some really good soft serve ice cream, as well as some of the best stuffed pizza in the area on Friday at The Tavern. It’s a quiet town, with friendly folks and plenty of outdoor activities across the area..

Guest favourite
An outdoor fire pit sits at the center of a gravel circle surrounded by several Adirondack chairs. The chalet, elevated on a wooden deck, features a welcoming front porch and an American flag. Lush greenery and trees provide a natural backdrop.
Chalet in Hensonville
4.95 out of 5 average rating, 102 reviews

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!

Top guest favourite
The A-frame structure is surrounded by lush greenery, featuring a thatched roof and large triangular windows that allow natural light to fill the interior. A gravel driveway leads to the front entrance, alongside a grassy area and a fire pit surrounded by stones.
Chalet in Hunter
4.95 out of 5 average rating, 130 reviews

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.

Top guest favourite
A coffee cup rests on a wooden table, overlooking a vast expanse of greenery and rolling hills under a cloudy sky. The scene captures a moment of tranquility with nature as a backdrop.
Chalet in Gilboa
4.98 out of 5 average rating, 171 reviews

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.

Guest favourite
The exterior of a Bavarian-style chalet is displayed, featuring a two-story structure with a steeply pitched roof and a front balcony. The surrounding lawn is adorned with seasonal foliage, and the mountains in the background are highlighted by autumn colors.
Chalet in Big Indian
4.95 out of 5 average rating, 174 reviews

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

Top guest favourite
Tall wooden walls frame large triangular windows, providing expansive views of rolling mountains and trees. Natural light floods the inviting living area, furnished with a dark leather sofa, light-colored ottomans, and green plants, creating a comfortable and spacious atmosphere.
Chalet in Prattsville
4.99 out of 5 average rating, 154 reviews

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.

Top guest favourite
A cozy wooden chalet is set amidst lush greenery, featuring a spacious front deck with wooden railings. Two blue adirondack chairs are positioned around a stone fire pit, inviting relaxation. The house's sloped roof and chimney complement the rustic aesthetic, surrounded by trees under a clear blue sky.
Chalet in East Jewett
4.98 out of 5 average rating, 108 reviews

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.

Guest favourite
An inviting great room features a wood-burning fireplace surrounded by natural stone. Expansive windows frame views of the outdoors, while warm wood beams and flooring enhance the cozy atmosphere. A mix of seating options, including a leather sofa and wooden chairs, create a welcoming gathering space.
Chalet in Windham
4.93 out of 5 average rating, 104 reviews

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!

Guest favourite
A charming chalet is set against a clear blue sky, featuring a spacious wooden deck that extends along the front. Large windows are framed by the light-colored exterior, while greenery surrounds the property, enhancing the natural landscape.
Chalet in Windham
4.96 out of 5 average rating, 133 reviews

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.

Top guest favourite
The A-frame house showcases a striking design with a steeply pitched roof and large windows. A spacious deck extends across the front, offering a place to relax. Surrounding trees provide a sense of privacy, and vibrant foliage adds color to the scene.
Chalet in Saugerties
4.98 out of 5 average rating, 170 reviews

A-Frame Chalet in the Heart of the Hudson Valley

Set back on a private road surrounded by tall trees, The Chalet is a three bedroom, three bathroom A-frame house in close proximity to all the main attractions of the Catskills and Hudson Valley. Perfect for a weekend getaway or an extended stay, and great for couples and families. The house has three levels, each with its own bedroom, bathroom and common area. Relax by the fire pit, sip morning coffee on the deck, read a book in the loft, or take a walk in the woods.

Guest favourite
The A-Frame chalet features a striking design with an orange and black exterior. A spacious patio area offers seating for relaxation, surrounded by lush green trees and a well-maintained lawn. A stone pathway leads to the entrance, providing a welcoming atmosphere.
Chalet in Hunter
4.95 out of 5 average rating, 191 reviews

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!

Top guest favourite
A back deck overlooks the scenic Catskill Mountain range, featuring a recessed hot tub and a fire pit. Soft lighting from string lights enhances the outdoor space, inviting relaxation while taking in gentle mountain views at sunset.
Chalet in Fleischmanns
4.99 out of 5 average rating, 242 reviews

Crows Nest Mtn. Chalet

Elevated into the Mountainside, Crow’s Nest looks out onto a spectacular view of the Catskill Mountain range of Belleayre. Grab a cup of coffee and watch the sunrise from the back deck or bask in the glow of the sunset while relaxing in the hot tub or hammock. This is an incredible place to unwind and take in that fresh mountain air or retreat to one of the many hangout spots in this newly renovated home. Follow us on IG : @crows_nest_catskills

Popular amenities for chalet rentals in Windham

Quick stats about chalet rentals in Windham

  • Nightly prices starting at

    Windham holiday rentals start at ₹24,595 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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