Chalet holiday rentals in Windham

An open floor plan living area features vaulted wooden ceilings and large windows offering views of the outdoors. Comfortable seating areas include a tan couch, black chairs, and a decorative coffee table. A dining space with a large table and an island kitchen is also visible.

4.97 out of 5 average rating, 154 reviews

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!

4.95 out of 5 average rating, 103 reviews

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

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!

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.

4.98 out of 5 average rating, 171 reviews

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

Chalet Near Windham w/ Panoramic Views on 22 Acres

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.

4.95 out of 5 average rating, 176 reviews

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

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

4.99 out of 5 average rating, 154 reviews

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

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.

4.98 out of 5 average rating, 108 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.

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.

4.93 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!

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.

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.

The octagonal log home is nestled among trees, with a flowing creek visible nearby. A spacious outdoor area features a hot tub and fire pit surrounded by seating. Scenic views of the landscape create a serene backdrop, showcasing natural beauty and tranquility.

4.91 out of 5 average rating, 386 reviews

Big Timber Lodge - Hunter Mountain’s TOP Getaway

Discover why our guests have left over 275 five star reviews! This 3-story custom log home sits perched on a beautiful running creek for the perfect weekend or midweek getaway. Featuring a premium outdoor hot tub, fire pit area and truly unforgettable views. Our home offers two units each with three bedrooms, kitchen, indoor jacuzzi, fireplace and plenty of games. The staircase to the creek brings you steps away from a meditative nature walk, trout fishing and zen relaxation.

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.

4.95 out of 5 average rating, 192 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!

5 out of 5 average rating, 211 reviews

A cozy outdoor space features a fire pit surrounded by wooden Adirondack chairs, creating an inviting ambiance. Soft outdoor lighting enhances the warm color of the chalet, which is complemented by a patio umbrella and lush greenery in the background.

Chalet in Tannersville

Catskill Chalet: Hunter Mtn Ski Chalet w/Spa

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! 😻

Popular amenities for Windham chalet rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly chalet rentals

An aerial view showcases the chalet's exterior surrounded by lush greenery. The large garden is visible with a gravel driveway leading to the entrance. Outdoor seating areas are arranged on the patio, complemented by a stylish deck overlooking the expansive lawn.

4.86 out of 5 average rating, 64 reviews

Rustic Mountain view Cabin 5 mins to Ski Area!

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

4.97 out of 5 average rating, 185 reviews

Chalet in Jewett

Catskills Chalet w/ Hot Tub | Near Ski Resorts

4.99 out of 5 average rating, 168 reviews

An aerial view showcases a secluded log home surrounded by lush green trees on a mountainside. The property features a pool and well-maintained landscaping, creating a serene natural environment. Rolling hills and forest are visible in the background, enhancing the sense of privacy and tranquility.

Chalet in Olivebridge

Spruced Moose Lodge w. Hot Tub & open Pool to oct

Chalet in Livingston Manor

The cabin features a wooden exterior, with a front deck supported by sturdy railings. Large windows provide views of the surrounding greenery, and a small balcony is visible above the entrance. The well-kept lawn extends around the house, enhancing the natural setting.

4.94 out of 5 average rating, 109 reviews

Cozy Catskills Chalet *Hot Tub*

5 out of 5 average rating, 84 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, 44 reviews

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

5 out of 5 average rating, 12 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.

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, 57 reviews

Blue Spruce Chalet — Hot Tub, Pet Friendly

4.96 out of 5 average rating, 205 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

4.95 out of 5 average rating, 109 reviews

A spacious chalet sits nestled among trees, showcasing a wraparound deck and multiple outdoor seating areas. Smoke gently rises from the fire pit area, indicating a cozy gathering. The natural landscape is vibrant with autumn foliage, enhancing the tranquil ambiance of the mountain retreat.

Chalet in Prattsville

Catskills 5BR • Near Windham/Hunter • Deck+Firepit

4.95 out of 5 average rating, 129 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/grill, firepit & mountain views

4.96 out of 5 average rating, 113 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, 109 reviews

Chalet in Elka Park

Thorne Hollow - Mountain Ski Getaway with HotTub

4.9 out of 5 average rating, 165 reviews

A unique three-story silo home is showcased, featuring a wooden exterior and numerous windows glowing warmly. Surrounded by snowy landscapes and trees, the structure is complemented by a wooden deck leading to an inviting red door.

Chalet in Willow

Cozy Silo Home w Mountain Views near Woodstock

4.95 out of 5 average rating, 101 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

Lakefront chalet rentals

A scenic view from a wooden deck showcases a tranquil lake surrounded by greenery. Bright, leafy trees frame the image as the calm water reflects the sky. Cozy seating is positioned on the deck, inviting relaxation in this serene outdoor space.

4.98 out of 5 average rating, 169 reviews

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

A cozy living area is highlighted by a comfortable sectional sofa, adorned with decorative pillows. Natural light floods in through a series of large windows, complementing the wooden walls and stone fireplace, which creates a relaxing atmosphere for gathering.

4.88 out of 5 average rating, 59 reviews

Large & Sunny Lakefront Home-kayaks/fire pit/games

A spacious lakefront home is nestled among tall trees, with a sloping green lawn leading to the deck. The house features a distinctive A-frame design with large windows, allowing natural light to fill the interior. Shadows from the surrounding trees enhance the serene outdoor setting.

4.88 out of 5 average rating, 121 reviews

Waterfront Lake Home, close to Hunter & Windham

5 out of 5 average rating, 4 reviews

Brand New Lakefront Retreat! Kayaks/Firepit/Games

5 out of 5 average rating, 12 reviews

The exterior of Maple Lodge showcases a modern grey house surrounded by greenery. A large deck features seating around a fire pit, while a children's play structure adds to the yard's charm. Ample parking is available in the gravel area beside the home.

Chalet in Lanesville

Maple Lodge - Luxury Cabin

An outdoor space features multiple white Adirondack chairs arranged around a firepit, surrounded by trees. Soft lighting enhances the serene atmosphere, with the calm waters of Sleepy Hollow Lake visible in the background, and a dock positioned along the water's edge.

4.96 out of 5 average rating, 52 reviews

Lakefront w/Dock! Kayak | Pools | Firepit | Games

The image depicts a lakefront property surrounded by lush greenery. A wooden dock extends into the water, with a variety of boats moored nearby. Red umbrellas provide shade on the lawn, enhancing the outdoor setting nestled among trees.