Vacation rentals in Windham

Gorgeous Modern Lodge w/ Mt View - 5 Min to Skiing

Plan your all-seasons escape to this gorgeous new mid-century modern chalet with can't-beat direct views of Windham Mtn, less than a 5 minute drive away. Situated between state land and an active creek, enjoy this mountain getaway's hot tub, firepit, game room, open floor plan and other luxury 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!

Designer Chalet with Sauna|Hot tub|Mountain View

Recognized as one of the Catskills’ most exclusive retreats, @lechaletcatskills is a modern-luxury escape where mountain serenity meets refined design. Set on 10 private acres near Hunter, Windham & Belleayre, this designer chalet invites you to unwind in style -think panoramic views, cedar sauna, hot tub under the stars & firepit for marshmallow nights. With a chef’s kitchen, curated interiors & nature all around, Le Chalet is the Catskills getaway your friends and family will be talking about.

Custom Catskills private retreat

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 :)

Hideaway Windham/Hunter Fireplace, Snow & Skiing

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Stay on Windham Mt- Mins to Main St + Hot Tub

A unique blend of architectural and design features, this home is one of a kind and perfect for your mountain getaway. The expansive 3800+ sq ft mountain retreat features 5 bedrooms, 5.5 bathrooms, and two large living areas, providing plenty of space to accommodate family & friends. There is also a brand new speakeasy bar to enjoy. Steps to the ski trail (or mountain biking) and hiking, golf, restaurants, and wedding venues, the location is ideal for all seasons. @AlpineLookout on IG

*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.

Catskills log cabin in the sky with mountain views

Welcome to Cabin in the Sky! At 1,671 ft elevation, Cabin in the Sky is a newly renovated log cabin nestled in the mountainside with tranquil views. The home offers the perfect combination of seclusion and convenience. In the mornings/evenings, enjoy a cup of coffee or glass of wine from the private deck which overlooks pure nature (not a car, street or building in sight). During the day, take advantage of the local hiking, skiing, farmer's markets, restaurants and shopping.

Riverfront, Fireplace, 20 min to Hudson & Windham

Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

Little Red Cabin Near Windham & Hunter w/ Hot Tub

Nestled in the woods, our 3 bedroom cabin offers the perfect escape from the hustle and bustle of everyday life. The cozy interior features a warm, inviting atmosphere with all the amenities you need for a comfortable stay. The spacious living room is the perfect place to unwind after a long day of exploring the great outdoors, complete with a cozy fireplace and outdoor hot tub that offer stunning views of the surrounding landscape. Follow us on IG @thelittleredcabinny

Windham Mountain Village 2 bedroom townhouse

This 2 bedroom, 2 bath Townhouse with loft that sleeps 8 (max 6 adults) is located at the top of Windham Mt Village a very short walking distance from the Windham ski lodge and beginner lifts. Fully equipped kitchen, dining area, living area with fireplace including firewood. TV with cable and free high speed wifi. Outdoor deck with gas grill. Washer and Dryer. 2 parking spots in front. Access to community pool and hot tub when open. Air Conditioning in summer.