Holiday houses in Windham

Pool |MTNView| HotTub |Sauna| Games|Movie| Firepit

Pool is Open April 1-October 15. Pool heating fee applies. SAUNA IS TEMPORARILY UNAVAILABLE RED FEATHER LODGE is an upscale, modern-mountain sanctuary offering elevated lodge luxury, postcard-perfect ski-slope views, and endless amenities for families, groups, and all-season adventurers. Set on six private acres of forest, meadows, and mountain scenery, this retreat blends natural wood, stone, soaring views, across three beautifully designed levels. Less than 10 minutes to Windham Mountain.

Cozy Modern: Views, 3 min ski, fire pit, game room

Welcome to Windy Hollow! A spacious and newly renovated vacation home with stunning views of Windham Mtn and a block to town. Thoughtfully designed to provide multiple gathering spaces for guests over two levels. We are ideally setup for families & groups. Ski the slopes, hike the trails, bike, golf, swim in the lakes, enjoy a winery, fancy the spa, visit our wonderful local restaurants. However you decide to spend your vacation, Windy Hollow offers a home-away-from-home experience year-around.

Catskills Designer Retreat near Hiking + Swimming

★ One of Airbnb’s Most-Loved Design Homes in the Catskills ★ Relax & recharge at Casa Magda—a design-forward retreat on 9 acres in Windham, just 2.5 hours from NYC. Perfect for design lovers and nature seekers, this renovated 1980s gem blends modern style w/peaceful seclusion. Unwind in the hot tub, cozy up by the fireplace w/a record, or gather around the firepit beneath star-filled skies. Explore nearby restaurants and trails, ski Windham Mountain 7 mins away or head to Hunter in 15 mins.

NEW Modern Cabin 8 mins from Skiing-Hot Tub & Gym

Immerse yourself in luxury at Timber Trail Lodge, an opulent 5-bedroom, 4 full bathroom estate nestled in Windham’s premier location. This expansive 4,000 ft² home offers the ultimate mountain escape, high-end amenities such as a modern spa, chef’s kitchen, Sonos, and an outdoor fire pit, perfect for entertaining. Adventure seekers can enjoy a private zip-line and proximity to Windham Mountain 8 minutes away. Timber Trail Lodge combines modern comfort, outdoor fun, and serene Mountain View’s

Villa Windham | 6BDRM, Pool, Hot Tub & Movie Room

A spectacular six-bedroom estate offering refined luxury and comfort. Nestled within the exclusive Dingley Dell Estate, it's just a six-minute drive to Windham town and about 25 minutes from Hunter Ski Resort. The property features expansive, beautifully landscaped grounds, inviting outdoor seating areas, a prime location, and exceptional privacy. Completely renovated for ultimate guest comfort, the home also includes a pool, movie room, premium sound system, and breathtaking mountain views.

Cozy Family-Friendly A-Frame - Windham with AC

Escape to this peaceful A -Frame mountain retreat in the Catskills. Windham is know as the “Gem of the Catskills” and was recently named as a big charm town and perfect for a weekend getaway in New York by World Atlas. Only 5 minutes from Windham Mountain with skiing and snowboarding, hiking, golfing, restaurants and shops. Relax and enjoy with the whole family and friends around the fireplace, game room, or large deck. We believe without a doubt you will love this home as much as we do!

Modern Ski House Minutes From The Slopes

This recently updated one of a kind Catskill ranch is 2.5 miles from main street Windham and 3.4 Miles to the Ski Windham. Three bedrooms, 2 baths, jacuzzi tub and a huge living room make the house perfect for hosting large groups comfortably. Wood burning fireplace, contactless check-in, new memory foam mattresses, monster bean bag chair, fire pit, gas grill and range and dedicated workspace for those working remotely. 1.5 acres of fenced land off the back door is perfect for pets!

Modern House with Mountain View @Getawind

Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Alpine Chalet on Spectacular Property

Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

Secluded Fernwood Chalet, Hot Tub, & Sauna House

Come immerse yourself in the beauty of the Catskills and enjoy the Fernwood chalet featuring mountain views and set upon 32 acres with private hiking trails, a hot tub, and a sauna house! Enjoy skiing in the winter (9 min. To Windham mtn., 18 to Hunter)hiking when it's warmer, fishing, swimming holes, lakes, you name it! Several wonderful dining options in the town of Windham, farmers markets & festivals, and other excursions a short drive away, or simply zen out at Fernwood!

Cozy Creekside Cabin | 5 Mins to Windham Mt!

Nestled in the hills of Windham NY, the Creekside Cabin is a hidden gem just under 2.5 hours from NYC. Ideal for families and small groups of friends, this cozy cabin features three bedrooms, one bathroom, a comfortable living room overlooking a tranquil creek, and a fully equipped kitchen with a wood-burning fireplace. Whether you're looking for a weekend escape or a longer retreat, the Creekside Cabin offers a peaceful and relaxing stay in a beautiful natural setting.

The Catskill Equestrian Cabin

Decompress in this beautiful, calm, serene new cabin build nestled in the mountains on a peaceful, private five acre lot, bordering an equestrian center. Walk less than two minutes to see the horses during your stay. The cabin is less than 15 minutes to Windham mountain for winter skiing and under 20 minutes to the popular town of Catskill. This cabin has all the amenities you need for a wonderful stay. We hope to host you soon!