Ski-in/Ski-out holiday rentals in Windham

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.

Hunter Mtn. Close Clean Cozy 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

Lake&Hunter Ski Resort Luxury Lodge/Hot Tub, Sauna

Award-winning luxury Lodge on Hunter Mountain, offering a private, resort-style escape. This immaculate 3-level retreat features a modern kitchen, open living spaces, cozy fire stove, and a spacious game room. Enjoy private lake access, unwind in the outdoor hot tub or authentic Canadian sauna, and take in stunning lake and mountain views from many wrap-around decks and balconies. Sleeps up to 20 guests, just 2 min from Hunter Mountain Resort entree, skiing, lifts, and year-round adventures.

Best value around, AC, sauna cozy 4 Bedroom 3 bath

Welcome to our cozy yet spacious four bedroom, three-bath (one with a clawfoot tub) retreat at the base of Hunter Mountain. We’re within walking distance of a movie theater, café, synagogue, and other local favorites with Windham Mountain just a short drive away. Unwind outdoors: enjoy a meal under the stars, gather around the fire pit, or rejuvenate in our brand-new outdoor sauna.Owner-managed with no cleaning fees, plus flexible check in/out whenever possible. Come relax and be our guest!

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 usually summer and winter. Air Conditioning in summer.

Catskill Cabin, Little Owl Apt #1 * * * * *

Little Owly Apartment at the base of Belleayre Mountain 🏔️ A cozy Catskills retreat with a secluded private porch Perfect for slow mornings, fresh air, and year round escapes 🌿 Natural fineness meets charming style. Thoughtfully designed for relaxed stays, with a focus on healthy living and connection to nature 🌱 Surrounded by miles of forest, enjoy mountain views, quiet moments, and the outdoors right outside your door 🦉 Follow @alpinefourseasonlodge No parties or events 🚫

Secluded Woodstock Retreat -Heated Pool and Sauna

Stunning, tranquil mountainside retreat with exposed beams, heated saltwater swimming pool, sauna, fireplace, soaking tub and rain shower. Situated on a 5-acre wooded hilltop, a ten minute drive to Woodstock and close to miles of walking trails. Roast marshmallows on the fire pit, flip burgers on the 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.

Sweet cottage near Hunter Mountain

This is our home away from home where we love to go in our free time. The house is 10 min drive from Hunter mountain or Windham. Great for skiing in winter / hiking in summer. WiFi: YES! High speed internet, Fiber Optic, 200Mbps. Perfect for work from home. Netflix, Disney+ and great selection of movies is available for all guests which you may enjoy on new 75 inch TV. Great for movie nights! Sound system through out the house is also available. Baby equipment upon request.

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.

Tivoli Star Gazing Cabin

Down a long driveway, set amongst 100 year old trees and meadows, the cabin offers time in the quiet country though only minutes to the lively village of Tivoli. With a wrap around porch for morning coffee, fire fly viewing or star gazing. It has a soaking tub, with a hand held shower. The cabin is part of our family compound of a main house and a small garden hut. Each property has an independent outdoor space for relaxing and privacy.

"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.

Cozy, peaceful-3Br (5 beds)2.5 Bath townhouse

A cozy townhouse 3 bdrm /2.5 bath in the center of the Catskills (Windham Mountain Village), this retreat is perfect for families, celebratory events or just a quiet nature getaway. From wineries to breweries, to zip lining and hiking, to admiring the many waterfalls, this area has something for everyone! PLEASE NOTE: POOL AND HOT TUB WILL BE CLOSED FROM SEPTEMBER 2 to NOVEMBER 27, 2025