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, 356 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, 245 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.

Superhost

A cozy living room features a brick fireplace as the focal point, surrounded by wooden shelving units. A modern light fixture hangs above, while a wall-mounted television is positioned for convenient viewing. A comfortable seating area invites relaxation and socializing in a welcoming setting.

Home in Jewett

4.85 out of 5 average rating, 108 reviews

Hunter & Windham

Awesome and fully renovated 3 bedroom 2 bath house right between Hunter and Windham mountains. Comfortably sleeps 6 people with extra room on a fold out sofa in front of a cozy fireplace. Enjoy company after a nice day spent in the nature and have fun with friends over a selection of board games or read an interesting book. It is a perfect place to sit back and relax on either front or back porches overlooking the peak of the Hunter mountain and presence of wildlife of the Catskills forest.

Top guest favorite

The entryway features wall-mounted storage cubbies made of natural wood, filled with various winter gear. A long wooden bench provides seating, coupled with neatly arranged ski and snowboard boots on the floor. A doorway leads to another room, visible in the background.

Home in Windham

4.94 out of 5 average rating, 102 reviews

Stay on Windham Mt- Mins to Main St + Hot Tub

A unique blend of architectural and design features, this home is one of a kind and perfect for your mountain getaway. The expansive 3800+ sq ft mountain retreat features 5 bedrooms, 5.5 bathrooms, and two large living areas, providing plenty of space to accommodate family & friends. There is also a brand new speakeasy bar to enjoy. Steps to the ski trail (or mountain biking) and hiking, golf, restaurants, and wedding venues, the location is ideal for all seasons. @AlpineLookout on IG

Superhost

A cozy living room features wooden walls and a vaulted ceiling. Comfortable seating is arranged around a rustic stone fireplace. Large windows allow natural light to fill the space, while a TV is mounted on the wall for entertainment.

Cabin in Prattsville

4.88 out of 5 average rating, 266 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, 126 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.

Guest favorite

Cabin in Lanesville

4.93 out of 5 average rating, 344 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, 100 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 light-filled living area features a white couch adorned with striped cushions. A wooden coffee table sits atop a textured rug, while a small potted plant and candles are arranged on it. Large glass doors lead to an outdoor view with vibrant autumn foliage.

Home in Germantown

4.97 out of 5 average rating, 352 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

The cozy living area features a green sectional sofa adorned with patterned cushions. Two orange accent chairs are positioned around a unique coffee table. A vintage wooden side table and a television set against a light wall complete the space, illuminated by warm overhead lighting.

Home in Phoenicia

4.93 out of 5 average rating, 176 reviews

Leaf Peepers. We are at peak! Heart of Phoenicia

Hey Leaf Peepers, Phoenicia is hitting full stride right now with glorious color. Don't wait to show up."Such a cute place with cabin-in-the-woods vibes but all the conveniences of being in town." What Shannon said in her 5 star review. Relax and reconnect in this calm and quiet little house nestled in the center of our cool village. Lounge around a glowing campfire in the back yard with S’mores or spin viny. On NYC bus route and ski shuttle.

Guest favorite

An outdoor area features a wooden deck with a covered seating area and patio furniture. A picnic table is positioned on the grass, with a pathway leading to steps that provide access to the yard. Nearby, a stone structure adds rustic charm to the space.

Home in Hunter

4.83 out of 5 average rating, 192 reviews

Cozy 3 bedroom summer winter home

This summer and winter retreat hosted by mark and jackie laskowski is perfect for summer fishing hiking biking swimming and all festivals and mtn jam walking distance to hunter mtn ski resort for all winter activities including skiing snowbording and tubing has deck with beautiful mountain views very clean has new windows furnace kitchen and bathroom new beds very warm and cozy with ample parking

Guest favorite

A spacious living area features comfortable seating arranged around a wooden coffee table. Natural light filters through a large window adorned with blinds, illuminating the room. A television is positioned on a wooden console, complemented by a floor lamp beside a cozy sofa.

Condo in Lanesville

4.9 out of 5 average rating, 118 reviews

Cozy Downtown Hunter Mountain Getaway

Keep it simple at my peaceful and centrally-located loft. You are at the footsteps of Hunter Mountain, right beside Dolan's Lake and a very short drive to all of Village of Hunter restaurants, bars, cafes, hikes and conveniences. You can easily walk to Hunter Mountain and the Trailways Bus line. The condo has its own wifi and 2 roku TV’s.