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"THE PAINTED COW" 5 acre farm in the mountains!!

"Come to nature" ALL FOUR SEASONS at our lovely renovated 1900s farmhouse set on 5 acres one mile from Windham Mountain Club. This vacation rental is perfectly suited for multi-family and friend getaways. Highlights: original artwork throughout, large country kitchen, cozy open bunk cove for kids, laptop workspaces. Outside: Starry skies, walking distance to Main St, wraparound porch, cozy evenings around the fire pit. Let the dogs and kids just run or cruise the Toboggan Hill on a snowy day.

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.

Europe in The Catskills

Welcome to "Europe in The Catskills", where your senses will commune with stunning nature and intimate surroundings, and where you will create enduring memories your family will cherish. Our European design is characterized by functionality, minimalism, and timelessness. With a neutral color palette, natural materials, functionality over form, and classic silhouettes, "Europe in The Catskills" beckons a culture of a morning espresso, an afternoon glass of Rosé, and embracing life with passion.

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

Windham Manor | 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.

Stargazing Dome|Sauna|Firepit|HotTub|Pet Frndly

Now featuring our brand-new GeoDome Lounge in Windham, NY Nestled in the heart of the Catskills, this Windham retreat is just 5 minutes away from Windham Mountain resort! Wake up to breathtaking views of Windham Mountain, with skiing, hiking, biking, and more just minutes away. After exploring, unwind in the hot tub, rejuvenate in the sauna, relax in the NEW dome lounge, walk around the 1.4-acre property, or gather around the fire pit. Our mountain escape invites unforgettable memories.

Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm

Plan your all-seasons escape to this beautiful, luxury chalet with direct views of Windham Mt., just a 5 minute drive to the slopes. Situated at the end of a private road on 3+ acres, enjoy this mountain getaway's hot tub, oversized deck, pond, firepit, huge game room, and other modern amenities. Just 2.5 hours from NYC, and minutes away to skiing (<5 min to Windham Mtn, 15 min to Hunter Mtn, 40 min to Belleayre Mtn), hiking, biking, swimming, golfing, fishing, vineyards and restaurants!

Slope Side Luxe | Views, Decks, Walk to Mtn & Town

This brand new 3600 sqft luxury condo, consisting of 5 bedrooms and 5 1/2 baths, is situated directly across from Windham Mountain. Private bathrooms for each bedroom. Large living space built for large groups with refined palates. Skiing and the adventure park are within walking distance. Close to mountain biking and hiking, and 1mi from golf at Windham Country Club. 1,000 sq ft of private decks to take in mountain mornings and unwind with a latte. Managed by Cedar Properties.

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.

EAT, DRINK, PLAY ... and Relax in Windham

Book your Fabulous GET-A-WAY with Family/Friends!!! From the exciting game room, to the tranquil firepit, to the open floorplan, you, your family & friends will have plenty of areas to gather or find peace & quiet. Our 3400 sq ft 5BR/3BA vacation home on 1.2 acres can accommodate your gathering of a few friends or a couple of families. Plus, we are close to dining, shopping, skiing, tubing, hiking, fishing, hunting, antiquing, town fairs, events at Windham and more.

Modern Forest Retreat with Hot Tub and Sauna

This spacious, serene and secluded chalet is a newly renovated four bedroom three bathroom luxury property - 7 minutes from Windham and 15 minutes from Hunter ski resorts. Take a peaceful walk in our 6 acre forest, read by a roaring fire, relax in the spa bath, or prepare a gourmet meal in the chef’s kitchen with double oven, wet bar and coffee station. Roast marshmallows at the fire pit as you star gaze and a nightcap in the hot tub will melt all your worries away!