Pet-friendly vacation rentals in Windham

Pawfect Family Retreat | Fully Fenced + Dog Park

Welcome to the Pawfect Family Retreat- our dog-focused cottage in East Durham, NY! This cozy 2BR, 1BA home with a loft (3rd BR /sleeping area) is made for tail wags and happy hearts. Enjoy a fully fenced backyard with a private dog park, pup-friendly amenities, and cozy spaces for the whole family. Just minutes to Zoom Flume. Close to Windham(13 mi) & Hunter Mountain(18 mi), hiking, farms, breweries, and antique shops, town of Catskill & Hudson-your year-round getaway for unforgettable memories.

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

"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.

Charming Home Lg/Mod Kit Hot Tub on Stream FirePit

Beautiful Country setting, Large fire pit across bridge next to beautiful stream w 6 Adirondack chairs,new stream side bluestone patio.2.6 miles from Ski Windham. Modern spacious kitchen Wolf &Sub Zero , Breville Barista espresso machine, comfy living rm with gas fireplace and 1906 antique player piano, flat screen smart TV. Large deck with stream view ,outdoor flat screen tv. Newly installed 6 Person Hot Tub w waterfall,2 person shower for relaxation after a hike. Gas fire table on deck also.

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.

Luxury Retreat-Heated Pool, Sauna, HotTub&C Plunge

Experience Catskills luxury at The Swan Home, a modern retreat designed by MPM Designs LLC. Newly renovated with high-end furnishings and curated outdoor living, it offers a private escape with heated pool, hot tub, cold plunge, sauna, open-air shower, and outdoor fireplace under the stars. Just 9 minutes to Hunter Mountain and 2 hours from NYC, with access to Woodstock, Rhinebeck, and Windham. Enjoy high-speed Wi-Fi, a home theatre, and designer finishes—perfect for a refined weekend getaway.

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

The Windham Cabin w/ Hot Tub

Cozy cabin minutes from Ski Windham, amazing restaurants, bars, and all seasonal activities! A true escape from city life, we welcome you to come and create memories with your friends and loved ones. There is a brand new Bullfrog Spa Jacuzzi installed on the deck in addition to a newly installed Culligan Water Filtration System. Brand new stainless steel refrigerator and stove, updated downstairs bath, wifi included, parking on premises, working indoor fireplace and so much more.

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!

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.