
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.
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.

Enchanted Woodstock Cottage with great hot tub
Stunning Woodstock home with great fireplace and outdoor hot tub in secluded wooded area yet only six minutes to the town of Woodstock! Near skiing,hiking and lakes. Cherry wood radiant heat floors, skylights and a stunning bluestone fireplace and piano. Three bedrooms- (two with queen beds/third room opens to deck with full-size bed. One bath. Thirty minutes to skiing! The indoor heated porch has amazing views, and the dining room is right off the kitchen, where you can enjoy beautiful meals.

Hunter Mtn. Cozy Close Clean Condo *Great Reviews*
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

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.

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

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.

Cozy Slope Side Retreat
Hunter Mountain Retreat nestled in the Trailside complex is steps from the slopes. During the ski season, you can walk through parking lot & ski down to get your lift ticket. The Kaatskill Mountain Club is on the opposite side of the trails where you can go for dinner or a drink at the bar. Activities include Zipline, Skyride, Disc Golf, Horseback Riding. Trailside is by far the best & most luxurious place to stay in Hunter. Our rates are very reasonable for the luxury & location.

Only Ski In Out on Mtn | Hike, Golf, Fish, Unwind
Slopeside 1 bedroom that fits 4! Enjoy the hiking within a 5 minute drive or just walk out onto the mountain from your porch. Access to seasonal community pool with unbelievable mountain views! 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.

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

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.

Catskill Cabin, Little Owl Apt #1 * * * * *
Natural fineness meets charming style. Follow us @alpinefourseasonlodge for connections, recommendations and the enjoy-full life. We focus on healthy living, the environment & sustainability. Every day something in nature, a bear in the bushes, picturesque autumn foliage perfect for hipsters and dudes, kids and us grownups. Enjoy the mountain views. The Lodge is surrounded by miles of forest land. Enjoy the mountain views. Parties or events are not allowed.

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!
Popular amenities for Windham ski-in/ski-out rentals
Ski-in/ski-out house rentals

True Ski-In/Ski-Out Cozy Family Trailside Chalet

ULTIMATE YEAR ROUND PLAYGROUND! Close to Hunter!

Dog friendly/Level 2 EV charger/Generator

Hunter's Top Rated Airbnb - Best Location Steps from Lodge

Cozy 3 bedroom summer winter home

30 minutes to Hunter Mountain

Beautiful Modern Mountain Retreat ~ Slope Side

Serene. Cozy. Close to all. Heart of Phoenicia
Family-friendly, ski-in/ski-out home rentals

SunFlower Suite at WoodPecker Hollow

Hunter Chalet 1 ml to Slopes Privately Convenient

Hunter & Windham

*Two Bedroom Lodge, 2 miles to Windham Mountain!*

The Little House

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

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

Windham Mountain Townhouse
Ski-in/ski-out cabin rentals

Fireplace + EV Charger: 8 mins to Belleayre

Best value in Hunter sauna cozy 4 Bedrooms 3 baths

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

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

The Bear’s Nest

Hunter Mtn Log Cabin w/ View

Hunter Haven/Luxury Cabin/Waterfall/River/Lake

Ski on ski off 4 BR Hunter Highlands Condo
Quick stats about vacation rentals that are ski-in ski-out in Windham

Total vacation rentals
Explore 30 vacation rentals in Windham

Nightly prices starting at
Windham vacation rentals start at G$27,188 GYD per night before taxes and fees

Verified guest reviews
Over 820 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Windham vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Windham rentals

4.9 Average rating
Windham stays are highly rated by guests—averaging 4.9 out of 5!
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- Ski-in/ski-out rentals Greene County
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- Ski-in/ski-out rentals United States
- Hunter Mountain
- Belleayre Mountain Ski Center
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Resorts World Catskills
- Windham Mountain
- Howe Caverns
- Thacher State Park
- Butternut Ski Area and Tubing Center
- Glimmerglass State Park
- Hunter Mountain Resort
- Plattekill Mountain
- Bash Bish Falls State Park
- Zoom Flume
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- Naumkeag
- Berkshire Botanical Garden
- June Farms
- Hancock Shaker Village
- Walkway Over the Hudson State Historic Park
- Poets' Walk Park
- Millbrook Vineyards & Winery




