Vacation rentals in Windham

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!

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.

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!

*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 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!

Alpine Chalet on Spectacular Property

Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

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.

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.

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.

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!