Pet-friendly holiday rentals in Windham

HiddenCatskillsCabin•PrivateTrails•River•SwimHole

Tucked away between Windham and Hunter, this cozy 3-bedroom cabin feels like your own secret mountain hideaway. Perfect for couples or small groups looking for a quiet Catskills escape. Mornings are slow, coffee tastes better here, and nights are for laughter, stories, and starry skies. Whether you’re hiking, or simply unwinding, this cabin offers that rare mix of warmth, comfort, and true Catskills magic. Outdoor enthusiasts heaven. River access through private trail . Epic summer vacation !

"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.

Luxurious Chalet w/ Incredible Views on 20+ Acres

A nature-lover's oasis, this 4 bed/3-bedroom/2-bath log-built chalet with contemporary furnishings is perched high along the northernmost edge of the Catskill Mountains offering unforgettable panoramic views from inside and out across 20+ secluded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Windam (7 mi), Hunter (16 mi), Catskill (26 mi) and Hudson (29 mi), this is the ideal location from which to explore the best the Catskills has to offer.

Le Chalet Catskills: Mountain View• Sauna• Hot Tub

Le Chalet Catskills is a modern, luxury mountain escape set on 10 private acres near Hunter, Windham, and Belleayre. Made for those who appreciate great design, style, and comfort, it’s the perfect place to create special memories with friends and family. Take in sweeping mountain views, unwind in the cedar sauna, soak in the hot tub under the stars, and gather around the firepit for cozy nights. With a chef’s kitchen and thoughtful interiors, it’s a Catskills getaway you’ll want to return to.

Private cabin in the Catskills

This is a 2 bedroom 1 bath house located just 7 minutes from the Windham ski mountain. The house is surrounded by scenic land with few neighbors to be seen. Skiing, fall foliage, swimming holes, hiking, golf, antiquing, horseback riding, local farms are just a few things to name that this area has to offer. The house itself is a true retreat, you will leave totally re-charged - sweet air, bird chirping, star gazing, grilling, bong fire or simply enjoy a few days of not seeing another soul :)

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.

Valley View Chalet: AC, Hot Tub, Firepit, Games

Spacious, peaceful lux cabin atop the Catskills. Enjoy mountain views and soak in the hot tub. Catch up in the vaulted room by the stone fireplace w/ a wide game selection, with a 2nd living room downstairs. Host a dinner party with our fully equipped kitchen. 20 mins to 6 towns. Visit breweries, antique shops, dine, hike, fish, golf, or relax. Great for groups, families, kids & pets. Fast 600mb internet, AC, EV charger, generator. WFH, newborn, pet friendly. 3+ nights get discounted rate

*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.

Secluded 55 acre Windham Getaway w/ 6BRs + Hot Tub

~~ One of the top rated AirBNBs in all of Windham. 4.98 with 100+ reviews ~~ The perfect ski and getaway home for groups of families, w/six large bedrooms that sleep 16+ comfortably. Nestled on 55 acres, our serene, sun-drenched home is just a few miles from the Slopes. Includes 3 full baths, an outdoor hot tub, game room, and a huge wrap around deck w/ propane grill. Create memories around our outdoor fire pit, or snuggle up at the fireplace in our spacious living/dining room.

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!

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Mountain-Modern 5BR Home • Windham & Hunter • EV

A 5 bedroom , spacious, 5-acre mountain modern home boasting all comforts and amenities you could need in the heart of the Catskills! The house is tucked away, secluded, meanwhile just minutes away from lakes, hike trails, golfing, ATV rentals, breweries, farmers markets, restaurants, vineyards, local shops and skiing or snowboarding at either Windham Mountain resort or Hunter Mountain! Welcome to GreeneHaus!