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.

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.

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!

The Windham A

Discover year-round comfort and style at this beautifully designed A-frame cabin just 5 minutes from Windham Mountain and 20 minutes from Hunter Mountain. With 3Beds, 3Baths, and a loft, this modern retreat is perfect for families, couples, or friends seeking a peaceful escape in the Catskills. Step downstairs to a fully finished basement that features a game room, private theater room, and a stylish bar area—perfect for après-ski gatherings, movie nights, or fun with friends and family.

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.

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!

Cozy Cottage Retreat Close to Main St/Windham Mtn

Welcome to Maplewood Cottage! Wake up to the beautiful sunshine and sounds of nature surrounded by several acres in beautiful upstate New York. It's the perfect place to relax and call home after spending a day hiking the many nearby trails of the Great Northern Catskills or shredding the slopes at Windham Mountain (4 min) or Hunter Mountain (17 min). Easily walk to Main Street (8 min) and grab some good eats at the many amazing options that Windham has to offer!

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!