Chalet vacation rentals in Windham

4.99 out of 5 average rating, 165 reviews

Chalet in Prattsville

Designer Chalet with Sauna|Hot tub|Mountain View

Recognized as one of the Catskills’ most exclusive retreats, @lechaletcatskills is a modern-luxury escape where mountain serenity meets refined design. Set on 10 private acres near Hunter, Windham & Belleayre, this designer chalet invites you to unwind in style -think panoramic views, cedar sauna, hot tub under the stars & firepit for marshmallow nights. With a chef’s kitchen, curated interiors & nature all around, Le Chalet is the Catskills getaway your friends and family will be talking about.

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.

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.

Superhost

A covered outdoor seating area features a sectional sofa alongside several colorful Adirondack chairs on a patterned rug. Decorative string lights are draped overhead, and firewood is stacked nearby, creating a cozy space for relaxation.

Chalet in Gilboa

4.89 out of 5 average rating, 122 reviews

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!!

The living room features a wall of large windows that offer views of surrounding mountains. A combination of leather and upholstered seating is arranged around a coffee table, with a light area rug underfoot. Wooden ceilings and natural light contribute to a spacious atmosphere.

4.98 out of 5 average rating, 151 reviews

Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm

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!

4.98 out of 5 average rating, 110 reviews

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

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.

4.97 out of 5 average rating, 227 reviews

A sleek, modern outdoor area features a table lightly dusted with snow, surrounded by illuminated string lights. The glass walls provide views of a snow-covered landscape with trees and a flowing river, creating a serene winter atmosphere.

Chalet in Shandaken

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

4.95 out of 5 average rating, 139 reviews

A modern cabin is situated on a hillside, showcasing a spacious deck with seating and string lights. The structure features large glass windows, allowing a view of the surrounding forest. A cozy fire pit is visible on the grass, inviting outdoor gatherings.

Chalet in Stamford

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.

4.96 out of 5 average rating, 108 reviews

A spacious living area features a stone fireplace as its centerpiece, surrounded by large windows that offer views of the greenery outside. A wooden dining table and comfortable seating arrangements are situated nearby, with warm wood accents enhancing the room's inviting feel.

Chalet in Hensonville

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

4.98 out of 5 average rating, 182 reviews

The log-built chalet is surrounded by lush greenery and rolling hills. A spacious porch wraps around the house, and a fire pit with seating is visible in the foreground, providing a welcoming outdoor space amidst the natural landscape.

Chalet in Gilboa

Modern Chalet w/ Panoramic 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.

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.

4.94 out of 5 average rating, 110 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!

4.98 out of 5 average rating, 177 reviews

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

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.

4.94 out of 5 average rating, 197 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!

Popular amenities for Windham chalet rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly chalet rentals

5 out of 5 average rating, 77 reviews

The timber frame chalet is showcased in the evening light, highlighting its expansive front porch and large windows. Surrounding greenery features an array of trees and shrubs, while a stone pathway leads to the entrance, creating an inviting aspect to the property.

Chalet in Hensonville

Hilltop Family Escape + hot tub, 4 min to slopes

4.89 out of 5 average rating, 64 reviews

A modern house is surrounded by lush greenery, featuring large floor-to-ceiling windows that reflect the natural light. An expansive deck with two seating areas leads to a staircase, inviting guests to explore the tranquil landscape. The serene atmosphere is enhanced by the evening sky.

Chalet in Elka Park

Hunter NY, Unique, Private Waterfall, Mountains

4.86 out of 5 average rating, 59 reviews

A two-story blue house is set against a backdrop of tall trees, with a balcony extending from the upper level. Two wooden Adirondack chairs are positioned around a small fire pit on the lawn, which is surrounded by a grassy area.

Chalet in Prattsville

Cozy Catskill Home Near Windham and Hunter

Superhost

The cabin is framed by lush greenery, showcasing a wooden structure with a sloping roof and a spacious front deck. The surrounding area features a well-maintained lawn, dotted with trees and shrubs, offering a sense of privacy and seclusion.

Chalet in Claryville

4.85 out of 5 average rating, 238 reviews

Secluded Cabin in Catskills Park on 20 acres

5 out of 5 average rating, 90 reviews

The exterior of Black Forest Haus is framed by lush greenery, with a welcoming sign prominently displayed. A stone pathway leads to the charming chalet, showcasing its traditional architecture and a red umbrella on the deck, inviting guests to enjoy the serene mountain surroundings.

Chalet in Big Indian

Black Forest Haus | Cozy • Authentic • Whimsical

The exterior of the chalet is showcased, featuring a large wrap-around deck and multiple windows that invite natural light. A fire pit surrounded by seating is visible, along with a swing set for children. Lush greenery frames the property, enhancing the sense of privacy.

5 out of 5 average rating, 45 reviews

Mountain Views-Game Room-Hot Tub-5 minutes to town

4.93 out of 5 average rating, 15 reviews

A serene view of a two-story chalet surrounded by greenery, featuring a spacious fire pit area with several Adirondack chairs. Large trees provide shade while a wooden deck with seating overlooks the yard. The warm sunlight highlights the brick and wood exterior of the house.

Chalet in Hensonville

Serene two-level Chalet, 3 minutes from Windham.

5 out of 5 average rating, 55 reviews

A private theater space features a 200-inch screen at the front, complemented by colorful, hexagonal wall designs. Soft, adjustable lighting highlights the room. A plush electric massage recliner is positioned for optimal viewing, ensuring comfort during movie nights.

Chalet in Jewett

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

Luxury chalet rentals

An aerial view captures the log chalet surrounded by vibrant autumn foliage. The large deck features warm lighting and a hot tub, while the driveway accommodates parked vehicles. The property is framed by lush greenery, providing a serene natural backdrop.

5 out of 5 average rating, 60 reviews

Blue Spruce Chalet — Hot Tub, Pet Friendly

4.96 out of 5 average rating, 207 reviews

A kidney-shaped pool is set against a sunlit patio, showcasing clear water with a mosaic stone border. The house features a sloped roof and large blue-framed doors leading out to the outdoor space, with a dining area and grill visible in the background.

Chalet in Catskill

Daydream Mountain Art-Chateau | Hot Tub & Pool

4.96 out of 5 average rating, 112 reviews

Chalet in Prattsville

5BR Catskills Retreat • Ski Close • Hot Tub

4.98 out of 5 average rating, 87 reviews

The Great Room features high vaulted ceilings supported by heavy beams. A wooden desk is positioned near large windows, offering views of the outdoors. Natural light floods the space, enhancing the wood accents and cozy seating areas, including a plush armchair and decorative light fixtures.

Chalet in Maplecrest

Secluded Catskills Designer Lodge - Windham/Hunter

4.93 out of 5 average rating, 165 reviews

The living area features a cozy L-shaped sofa and an armchair, complemented by a unique hanging fireplace. Large windows allow natural light to illuminate the space, while a circular wooden coffee table adds warmth. A stack of firewood is neatly arranged nearby.

Chalet in Leeds

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

4.96 out of 5 average rating, 114 reviews

The living area features a high vaulted ceiling with exposed wooden beams. Soft sofas are arranged around a glass coffee table atop a plush, white area rug. Large windows invite natural light, creating an open and airy feel, with glimpses of the surrounding nature.

Chalet in Mount Tremper

Modern Mountain Chalet on 15 Acre Catskills Estate

4.97 out of 5 average rating, 114 reviews

Chalet in Elka Park

Thorne Hollow - Mountain Ski Getaway with HotTub

4.95 out of 5 average rating, 107 reviews

An aerial view showcases a secluded lodge nestled among a vibrant forest, displaying a spectrum of autumn colors. The spacious property is surrounded by trees and mountains, providing a serene and picturesque natural backdrop.

Chalet in West Kill

Charming & Private Catskill Chalet

Other chalet vacation rentals

5 out of 5 average rating, 24 reviews

Clearview Mt House • 2 Mins to Ski on Hunter Mt

5 out of 5 average rating, 41 reviews

A spacious living area is highlighted by a vaulted wooden ceiling and large windows offering mountain views. Two armchairs and a sofa are positioned around a circular coffee table, while a sleek wood stove adds warmth to the space, creating a welcoming environment.

Chalet in Fleischmanns

The Borderless Retreat Chalet

4.97 out of 5 average rating, 30 reviews

A large wooden house rests among snow-covered ground and bare trees, showcasing an expansive deck with railing. The structure features multiple levels and large windows, allowing natural light to fill the interior. Shadows from nearby trees create a natural pattern on the snow.

Chalet in Roxbury

Blissful secluded chalet with an epic view

4.87 out of 5 average rating, 23 reviews

The exterior of the chalet is highlighted by a wraparound deck adorned with hanging flower baskets. Plush greenery surrounds the property, complemented by a well-maintained lawn. Nearby, a garage and a white vehicle are visible, enhancing the tranquil outdoor setting.

Chalet in Roxbury

Modern Rustic Log Chalet w/ pool on 17 acres

The exterior of a two-story chalet is showcased at twilight, framed by lush greenery. Bright windows reflect the colorful sunset, and a spacious deck offers ample outdoor seating. The property is surrounded by a well-maintained lawn, enhancing the natural setting.

5 out of 5 average rating, 27 reviews

<5 Mins Ski Hunter | Apré, Hot Tub, Sauna, Sunsets

The exterior of a spacious multi-level home is illuminated by soft lighting, highlighting its vibrant red wood siding. A large deck features comfortable seating, overlooking a stone fire pit surrounded by Adirondack chairs. Lush greenery and trees create a serene backdrop.

5 out of 5 average rating, 11 reviews

Windham Views | Hiking | Game Room | Hot Tub

4.84 out of 5 average rating, 32 reviews

An open living area features vaulted wooden ceilings and large windows that allow natural light to fill the space. A cozy couch is arranged around a round coffee table, with a propane fireplace and TV positioned on opposite walls. Sliding glass doors lead to an outdoor balcony.

Chalet in Roxbury

Family Retreat with Hot Tub, Massage Chair, & More

The log chalet is illuminated under a clear night sky filled with stars. Warm light glows from the windows, highlighting the wooden structure, while trees surround the property, enhancing its secluded feel.