
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.

Only Ski In Out on Mtn| Hike, Golf, Fish, Recharge
Slopeside 1BR cabin sleeps 4! Step right onto Hunter Mountain from your porch or drive 5 min to scenic hiking trails. Prime location near the charming, colorful village of Tannersville. Enjoy a fully stocked kitchen & bath, high-speed WiFi, and an entertainment system with Netflix & all your other favorite streaming! Stay longer with the convenience of a W/D & dishwasher. Cozy up by the fireplace, take in the mountain views, or explore nearby dining, breweries, and outdoor adventures year-round!

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.

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

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.

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.

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!

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!

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.

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

Twin Peaks in the Catskills

ULTIMATE YEAR ROUND PLAYGROUND! Close to Hunter!

Free EV charging/Generator/Pet friendly

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

Catskills/Hunter Getaway w/new Kitchen/EV Charger

Abigail's Country Catskill House.

Charming Cozy Cottage Near Belleayre

Beautiful Modern Mountain Retreat ~ Slope Side
Family-friendly, ski-in/ski-out home rentals

Rubystar Haven~ rejuvenate in your tranquil escape

Hunter Chalet 1 ml to Slopes Privately Convenient

Hunter & Windham

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

Clearview Mt House • 2 Mins to Main • Hike & Swim

Luxury Ski in Ski out Condo + Amenities

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

Apartment just Steps from Ski, Restaurants, Bars
Ski-in/ski-out cabin rentals

Best value rental in town cozy 4 Bedrms 3 baths

Hillside Hideaway: fireplace + 5 mins to Belleayre

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

The Bear’s Nest

Hunter Mtn Log Cabin w/ View

Hunter Haven/Luxury Cabin/Waterfall/River/Lake

The Riverside - Hunter Mountain/Waterfront/Fishing

4BR ski on ski off Hunter Mountain Highlands Condo
Quick stats about vacation rentals that are ski-in ski-out in Windham
Total rentals
30 properties
Nightly prices starting at
$130 before taxes and fees
Total number of reviews
780 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
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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
- Minnewaska State Park Preserve
- John Boyd Thacher State Park
- Howe Caverns
- The Kartrite Resort & Indoor Waterpark
- Glimmerglass State Park
- Resorts World Catskills
- Bash Bish Falls State Park
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Windham Mountain
- Norman Rockwell Museum
- Taconic State Park
- Plattekill Mountain
- Opus 40
- Hunter Mountain Resort
- Albany Center Gallery
- Berkshire Botanical Garden
- Peebles Island State Park
- Hancock Shaker Village
- Huck Finn’s Playland, Albany
- Pineridge Cross Country Ski Area
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