Ski-in/Ski-out vacation rentals in Windham

Find and book unique ski-in/ski-out homes on Airbnb

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

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Hunter

4.96 out of 5 average rating, 493 reviews

*Great Reviews* Hunter Mtn. Close Cozy Clean Condo

Village of Hunter clean, cozy studio condo featuring vintage decor. Short walk to Ski Slopes, Snowtubing, Scenic Skyride, Dolan's Lake/Beach, Pickle Ball & Basketball Courts, Schoharie Creek, Fly Fishing, Hiking, Disc Golf, Stores, Eateries & Trailways Bus Stop. Murphy bed w/ full size comfy Casper Mattress, sectional couch, kitchen, microwave, electric wood stove, dinette, full bath, WiFi, Smart TV (no cable) w/Netflix, HBOGO, Pandora. No Pets/No Smoking or vaping in or on the property. Thanks

Top guest favorite

Condo in Hunter

4.96 out of 5 average rating, 251 reviews

Mint*Cozy*Ski In/Out*Hunter Mt Condo w/Fireplace

Best Ski In/Out Location steps to Ski Lifts & Base Lodge! Immaculate, Spacious with Beautiful Views of Hunter Mnt. All Winter Activities Right there: Skiing, Snowboarding, Snow Tubing. ~Enjoy a Private Deck w/2 Lounge Chairs ~Full Kitchen ~Winter Gear Outdoor Closet ~Front Parking Pass Other Nearby Attractions: Zipline, Skyride, Kaatskill Club, Kaaterskills Falls. Top Safety & Cleanliness: -Self Check-in/out -AirFilter Unit w/UV-C Light & Ionizer -Diffuser w/Essential Oil -Deep Sanitizing

Guest favorite

Chalet in Mount Tremper

4.98 out of 5 average rating, 145 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.

Guest favorite

Cabin in Lanesville

4.94 out of 5 average rating, 298 reviews

Exclusive Pool, Mtn Views! Hike, Golf, Swim, Relax

Mountainside 1 bedroom cabin that fits 4! Enjoy hiking within a 5-minute drive or walk right onto the mountain from your porch. Exclusive access to a seasonal pool with stunning mountain views (Memorial Day–Labor Day). 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.

Guest favorite

Home in Big Indian

4.98 out of 5 average rating, 185 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.

Guest favorite

Home in Phoenicia

4.93 out of 5 average rating, 163 reviews

Heart of Phoenicia: Serene. Cozy. Close to all.

"Such a cute place with cabin-in-the-woods vibes but all the conveniences of being in town." What Shannon said in a 5 star review after her stay. I couldn't put it better. Relax and reconnect in this calm and quiet little house nestled in the center of our cool village. You're on the doorstep of hiking trails with BREATHTAKING VIEWS and gorgeous trout streams. Lounge AROUND A GLOWING CAMPFIRE in the back yard with S’mores or SPIN VINYL. On NYC bus route and ski shuttle.

Guest favorite

Cabin in Prattsville

4.91 out of 5 average rating, 233 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

Guest favorite

Townhouse in Windham

4.9 out of 5 average rating, 117 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

Home in Hunter

4.83 out of 5 average rating, 190 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

Top guest favorite

Cabin in Jefferson

5 out of 5 average rating, 479 reviews

"Far from the Madding Crowd" Cozy Cabin Retreat

Cabin Clack is a quiet, stream-side retreat bordering 1000 acres of wild trails in NY State Forest. The cabin is a historic hunting cabin from circa 1935. The cabin is good for a couple, solo adventurers, or families (with kids). We welcome pets, and they will love exploring the secluded forest and the freedom of our virtually traffic-free dead-end road. There is a spring fed pond you can swim in.

Superhost

Home in Hunter

4.75 out of 5 average rating, 101 reviews

Beautiful 3 bedroom walkable to Mtn, creek & lake

Located only half a mile from Hunter's ski lodge and lifts! Whether you are in Hunter for the summer festivals or winter skiing, our historic once-upon-a-time Rail Road station offers the best of Hunter Mountain. Enjoy beautiful mountain views while being walking distance from Hunter's Main Street, lake and creek. This location is perfect for year round activities.

Guest favorite

Cabin in Hunter

4.95 out of 5 average rating, 154 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.