Ski-in/Ski-out rentals near Windham Mountain

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Top-rated ski-in/ski-out rentals near Windham Mountain

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Guest favorite
A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.
Home in Woodstock
4.94 out of 5 average rating, 363 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Top guest favorite
The farmhouse is set amidst lush greenery, surrounded by trees. A spacious yard features a deck and seating area, while a driveway accommodates parked vehicles. The exterior displays a combination of white siding and a tall stone chimney, blending harmoniously with the natural landscape.
Home in Lanesville
4.93 out of 5 average rating, 252 reviews

Roseland, Streamside 1865 house. 7 min to slopes

This beautiful streamside 1865 farmhouse is a magical, spiritual, mountain Utopia, located between historical Phoenicia and Hunter Mountain. This landscaped property is nestled in the heart of the mountains. Awaken and revitalize to the soothing sound of the beautiful, trout filled, Stoney Clove Creek, located at the end of the spacious backyard. Turn off your cell, get away from the stress and pressures of life, and experience what the ancient Indians once called, the magic of the mountains.

Top guest favorite
A wooden exterior is complemented by solar panels on the roof, showcasing sustainability. Surrounding foliage displays autumn colors, with trees and shrubs framing the entrance. The home features a welcoming porch area leading to large glass doors that invite guests inside.
Chalet in Mount Tremper
4.98 out of 5 average rating, 155 reviews

Secluded Woodstock Retreat with Pool and Sauna

Stunning, tranquil mountainside retreat with exposed beams, saltwater swimming pool, sauna, fireplace, soaking tubs and rain shower. Situated on a 5-acre wooded hilltop a ten minute drive from Woodstock and close to miles of walking trails. Roast marshmallows on the fire pit, flip burgers on the top of the line charcoal grill, and enjoy one of the best stargazing spots around. Indoors, find a well equipped kitchen and cinema sized tv screen with Netflix/Apple TV. Convenient to ski slopes.

Top guest favorite
The cabin's inviting exterior is illuminated by warm lights at dusk, featuring a spacious wrap-around porch with rustic charm. A wooden welcome sign and decorative wagon wheel enhance the country aesthetic, surrounded by pristine greenery and tall trees.
Cabin in Hunter
4.99 out of 5 average rating, 107 reviews

Best value rental in town cozy 4 Bedm 3 bath sauna

Welcome to our cozy yet spacious four-bedroom, three-bath (one with a clawfoot tub) retreat at the base of Hunter Mountain. We’re within walking distance of a movie theater, café, synagogue, and other local favorites with Windham Mountain just a short drive away. Unwind outdoors: enjoy a meal under the stars, gather around the fire pit, or rejuvenate in our brand-new outdoor sauna.Owner-managed with no cleaning fees, plus flexible check in/out whenever possible. Come relax and be our guest!

Guest favorite
An open living space features a stone fireplace at its center, flanked by large windows that provide natural light. Comfortable seating is arranged around a coffee table, and a dining area with chairs is visible in the background, all designed with rustic cedar beams overhead.
Home in Big Indian
4.98 out of 5 average rating, 190 reviews

Contemporary MOUNTAINSIDE home

The contemporary mountain side house is located between Woodstock and the Belleayre Ski Resort. Designed by an award winning architect, featuring cedar beams, vaulted ceiling, and walls of windows. Lower level houses the media/billiards room and 4 en-suite bedrooms all with individual private outdoor patios. Close to Peekamoose and Zephyr restaurants. Few minuets from Phoenicia and a little further is the historic Town of Woodstock with its long history in the arts and music.

Superhost
An outdoor seating area is presented alongside a hot tub and a fire pit. The seating features a sectional sofa with light-colored cushions. Dividing panels with a leaf design create a sense of privacy, while surrounding trees provide a natural backdrop.
Cabin in Prattsville
4.88 out of 5 average rating, 278 reviews

Little Red Cabin Near Windham & Hunter w/ Hot Tub

Nestled in the woods, our 3 bedroom cabin offers the perfect escape from the hustle and bustle of everyday life. The cozy interior features a warm, inviting atmosphere with all the amenities you need for a comfortable stay. The spacious living room is the perfect place to unwind after a long day of exploring the great outdoors, complete with a cozy fireplace and outdoor hot tub that offer stunning views of the surrounding landscape. Follow us on IG @thelittleredcabinny

Top guest favorite
The exterior view showcases two townhouse units set against a backdrop of rolling hills and clear blue skies. A sprawling lawn, dotted with trees, provides open green space. Features include a stone pathway leading to the units and a fire pit area visible in the distance.
Townhouse in Windham
4.9 out of 5 average rating, 130 reviews

Windham Mountain Village 2 bedroom townhouse

This 2 bedroom, 2 bath Townhouse with loft that sleeps 8 (max 6 adults) is located at the top of Windham Mt Village a very short walking distance from the Windham ski lodge and beginner lifts. Fully equipped kitchen, dining area, living area with fireplace including firewood. TV with cable and free high speed wifi. Outdoor deck with gas grill. Washer and Dryer. 2 parking spots in front. Access to community pool and hot tub when open. Air Conditioning in summer.

Top guest favorite
Cabin in Lanesville
4.94 out of 5 average rating, 363 reviews

Only Ski In Out on Mtn | Hike, Golf, Fish, Relax

Mountainside 1 bedroom cabin that fits 4! Ski on/off Hunter Mountain right from your doorstep. Enjoy hiking within a 5-minute drive or walk right onto the mountain from your porch. Unbeatable location on Hunter Mountain, short drive to the picturesque, colorful village of Tannersville, majestic Kaaterskill Falls, and renowned fishing! Fully stocked kitchen/bathroom, full entertainment system with streaming, high-speed WiFi, and dedicated work space.

Top guest favorite
The cabin is framed by expansive green grass and trees, with a large wooden deck extending from its side. Sunlight streams over the neighboring hills, while a flag is displayed in front of the cabin, creating a warm and inviting scene.
Cabin in Fleischmanns
4.97 out of 5 average rating, 105 reviews

The "Hog" Cabin. Year round perfect stay.

Less than two and a half hours from NYC, ten minutes from Belleayre Ski Center, this cozy and private cabin is perfect for a romantic couples retreat, two couples, a small family, or a group of friends looking for a relaxing and quiet escape. *High-Speed Broadband Wi-Fi Internet now provided* Feel free to roam the apx 2. 5 acres surrounding the property and enjoy the mountain views. Enjoy a nice cup of wine by the fire. You will absolutely love it!

Top guest favorite
A bright living space features a white sofa with light striped cushions, complemented by a wooden coffee table. A dining area with a light wood table and chairs is present. Large glass doors open to a scenic outdoor view, enhancing the open and airy ambiance.
Home in Germantown
4.96 out of 5 average rating, 363 reviews

Private Cottage/Mountain Views/Trails/Fire pit

A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ A Charming Gas Fireplace/ Fully equipped Chef's kitchen/Soapstone countertops/New premium appliances. Total Privacy High ceilings, hand plastered walls, antique doors. Glass French doors open to a private deck Enjoy big Catskill Mountain and seasonal Hudson River views. The large bath has a tiled glass door shower and a soaking tub. A Fieldstone fire pit overlooks the Catskills!

Guest favorite
A cabin is nestled against a backdrop of snow-covered hills and trees, showcasing a rustic wooden exterior. Two windows are visible on the upper level, while the surrounding landscape is blanketed in fresh snow, enhancing the serene winter atmosphere.
Cabin in Fleischmanns
4.89 out of 5 average rating, 111 reviews

Fireplace + EV Charger: 8 mins to Belleayre

A peaceful retreat in the Catskills on 14+ acres! Just minutes from Belleayre Moutain. Fleischmanns, Arkville, Margaretville, Phoenicia, and Roxbury. Ski/snowboard at Belleayre Ski Center or nearby Plattekill Mountain, hike the property and discover Emory Brook, visit local farmers’ markets, go fly fishing or tubing on the Esopus, or just relax, grill out and enjoy the fireplace. We want to share our cabin in the Catskills with you!

Guest favorite
The exterior of the home is shown, featuring a large deck with wooden railings. Surrounding greenery includes trees and shrubs under a bright sky. The house has multiple windows and a rustic wood facade, blending harmoniously with the natural landscape.
Cabin in Hunter
4.95 out of 5 average rating, 166 reviews

Log Cabin with view Ski Slopes in Hunter Mountain

Winter is quickly approaching and we couldn't be more excited to hit the slopes at Hunter Mountain & Windham! Step out onto the deck, take a deep breath while your coffee mug warms up your hands and open your ears to the therapeutic sound of the stream right from your backyard. Our home screams peace and quiet and is waiting for YOU.

Popular amenities for ski-in/ski-out rentals near Windham Mountain