Vacation rentals in Windham

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.

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

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!

CozyCatskillChalet w/ Hot Tub (Catskill Mountains)

At face value, IG: @cozycatskillchalet appears to be just a humble little getaway tucked in the Catksill Mountains of Windham, NY. But even the most discerning guests will be quickly spirited away by the rustic charm and postcard-eqsue surroundings all around. At night, can't-be-beat stargazing on the back deck (or while soaking in the hot tub) will have you convinced this humble hideaway is a lot more illustrious than it lets on. Disclaimer: The chalet is not a luxury hotel or property.

Wake Up to Mountain Magic Year-Round (Hot Tub)

Where Comfort Meets the Catskills. Relax and savor your coffee on the deck while the sun comes up over Hunter, just a few minutes away from Windham (7 min) and Hunter (8 min) with breathtaking mountain vistas. End the day by the fire pit for stargazing and s'mores. Indulge in the hot tub on the secluded deck with those mountain views. Have a blast all year round with hiking, swimming, kayaking, and fishing at nearby lakes. Fantastic dining and shopping choices await in Hunter and Windham.

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!

*Farmhouse Chic with Mountain and Lake Views*

Welcome to Bright Sparrow Farmhouse! Located on 8 acres of private land with greenery and a wetland lake, this home is the perfect spot to reconnect with nature and enjoy quality time with loved ones. Just mins from Windham and Hunter mountains. Enjoy skiing, hiking, biking, zip lining, water park, lakes, dining, and winery. Our home is a sustainable retreat, powered by solar energy and equipped with a backup battery system. This means you'll enjoy a comfortable and uninterrupted stay.

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!

Creekside Couple's Retreat w/Hot tub, Sauna & More

Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

The Mad Brook House | Walk to Main St, Windham

Walk to Main Street from this cozy Catskills cottage by the brook! The Mad Brook House is a newly refreshed two-bedroom, one-bath retreat in the heart of Windham — perfect for couples, small families, or friends visiting the mountains. Dating back to 1940, the home has been beautifully updated to combine classic Catskills character with modern comfort. Relax beside the gentle brook just steps from your door, or stroll to Main Street for dining, shopping, and coffee!