Ski-in/out vacation rentals in Windham

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

Top-rated ski-in/out rentals in Windham

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

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Guest favourite

Cabin in Lanesville

4.94 out of 5 average rating, 188 reviews

Catskill Oasis: The Only Ski In Ski Out on Mtn!

Slopeside 1 bedroom condo that fits 4! Enjoy the hiking within a 5 minute drive or just walk out onto the mountain from your porch. Unbeatable location on Hunter Mountain, short drive to town picturesque colorful village of Tannersville, majestic Kaaterskill Falls with hiking trails, and renown fishing! Fully stocked kitchen/bathroom, full entertainment system with Netflix and all of your favorite streaming services. Work from home with our high speed wifi connection and dedicated work space.

Nov. 5 – 12

$381 CAD per night

Guest favourite

Apartment in Windham

5.0 out of 5 average rating, 7 reviews

Main Street, USA in Windham, NY

The perfect base to explore Windham & spend time in the mountains. This immaculate 1 bdrm is located where Main St. begins. Walk to restaurants. Close to wedding venues-Windham Manor, Wylder Hotel & Hayfield. New Queen bed & L.R. sofa, open concept EIK/Liv. Rm, AC, Full Bath, Balcony. Only 0.7 mi. to Windham Mtn. entrance & 9 mi. to Hunter. Near Hiking Trails/Golfing/Music/4th of July parade&The Autumn Affair. WIFI. Smart TV/NO CABLE. Free LG & Pluto. Bring your Roku/Amazon/Netflix/Hulu codes.

Sep. 23 – 30

$147 CAD per night

Guest favourite

Guest suite in Hunter

4.98 out of 5 average rating, 102 reviews

Hunter Mtn Fully Private BR and Bath, Ski on/off.

Ski on/off. Private lock-out bedroom suite with full bath. Walk to: Hunter Mountain Festivals, sky ride, hiking, mountain biking, snow tubing, Dolan Lake, Schoharie Creek Swim Holes. Short drive to North Lake, Kaaterskil Falls, Movie Theaters, Arts Center, Westkill Brewery, Golf, fly-fishing, kayaking, snow mobiles, festivals and scenic road biking. Great Restaurants! Meticulously clean, smart TV, microwave, Keurig and medium refrigerator. Air Conditioning. Storage locker and on-site parking.

Jul. 23 – 30

$197 CAD per night

Guest favourite

Condo in Hunter

4.97 out of 5 average rating, 427 reviews

*Great Reviews* Hunter Mtn. Clean/Close/Cozy Condo

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

Jul. 15 – 22

$141 CAD per night

Guest favourite

Guesthouse in Germantown

4.94 out of 5 average rating, 309 reviews

The Studio at Pear Farm

This impeccably appointed large studio has gorgeous light and Catskill Mountain Views. Formally an artist studio, it has undergone an elegant and complete renovation. The luxurious bathroom features premium tile and a glass walled shower. The kitchen is new and nicely equipped. Enjoy outdoor grilling and dining on the private deck. The studio is located on 65 pristine acres fronting directly on the Hudson River. 5 minutes to Germantown. 10 minutes to Tivoli, Hudson or Bard College.

Aug. 31 – Sep. 7

$250 CAD per night

Guest favourite

Condo in Hunter

4.96 out of 5 average rating, 227 reviews

Mint*Cozy Ski On/Off Hunter Mt Condo w/Fireplace

Spacious Best Ski In/Out Location, Steps to Ski Lifts, Base Lodge & Kaatskill Club w/Restaurant, Bar, Wedding Venue. -Skiing, Snowboarding, Snow tubing all right there! ~Private Deck w/2 Lounge Chairs ~Queen Bed in Bedroom ~Queen Pull out Couch in Livingroom ~A Comfortable WorkSpace ~FREE Parking Nearby: *Restaurants *Bus Stop *Brewery *Hiking & Waterfalls Top Safety/Cleanliness: -Self Check-in/out -AirFilter Unit w/UV-C Light & Ionizer -Diffuser w/Essential Oil -Deep Sanitizing

Aug. 2 – 9

$464 CAD per night

Guest favourite

Condo in Lanesville

4.92 out of 5 average rating, 114 reviews

The Views! Beautiful Hunter Mtn. 1BR.

This is THE location on Hunter Mtn. Ski and hike the best trails from the backyard! Take in mountain views from deck. Decorated in modern ski decor that celebrates all 4 beautiful seasons. Maximize all of your mountain time, with this Liftside condo and enjoy apres ski & the many other area activities. Cable, wifi, gas fireplace. Work-space which includes a desk and monitor hook up. Clean linens/towels, coffee bar, laundry. Stocked kitchen & bath. Board games galore. Guide books.

Jun. 11 – 18

$234 CAD per night

Guest favourite

Home in Phoenicia

4.94 out of 5 average rating, 144 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 recent 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.

Jul. 23 – 30

$370 CAD per night

Guest favourite

Cabin in Prattsville

4.91 out of 5 average rating, 161 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

Feb. 26 – Mar. 5

$384 CAD per night

Guest favourite

Condo in Hunter

4.98 out of 5 average rating, 536 reviews

Hunter Mtn Liftside Ski In/Out, Slopeside!

Fantastic location! Liftside! Beautifully renovated SLOPESIDE ski on/ski off condo . Spacious one bedroom condo with fully stocked kitchen, luxurious bathroom with jacuzzi tub, large bedroom with queen bed, and comfortable, cozy open concept living and dining room. Real wood burning fireplace. Private deck backs up to the ski slopes at Hunter Mountain! Seconds away from the Kaaterskill Flyer lift , main lodge, and bar. Avail for seasonal rental 11/15-4/15 $15000

Aug. 26 – Sep. 2

$194 CAD per night

Guest favourite

Townhouse in Windham

4.88 out of 5 average rating, 99 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. Air Conditioning in summer.

Nov. 7 – 14

$224 CAD per night

Guest favourite

Cabin in Jefferson

5.0 out of 5 average rating, 432 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.

Jun. 12 – 19

$156 CAD per night