Holiday rentals in Windham

Gorgeous Lodge | Mt View, HotTub, Firepit, Game Rm

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!

Cozy Modern: Views, 3 min ski, fire pit, game room

Welcome to Windy Hollow! A spacious and newly renovated vacation home with stunning views of Windham Mtn and a block to town. Thoughtfully designed to provide multiple gathering spaces for guests over two levels. We are ideally setup for families & groups. Ski the slopes, hike the trails, bike, golf, swim in the lakes, enjoy a winery, fancy the spa, visit our wonderful local restaurants. However you decide to spend your vacation, Windy Hollow offers a home-away-from-home experience year-around.

Hot Tub | Sauna | Mountain Views | Fire Pit

Dreaming of the ultimate Catskills summer getaway? Set on 5 private acres, this is the perfect escape where comfort, luxury & adventure meet. Take in panoramic mountain views while lounging on the spacious deck or rejuvenating in the barrel sauna. Gather under the stars, unwind by the warm glow of the chiminea fire & soak in the hot tub. With hiking, mountain biking, swimming and charming towns just minutes away, create unforgettable memories - book today! Windham (10min) Tannersville (15min)

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.

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.

*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.

Slope Side Luxe | Views, Decks, Walk to Mtn & Town

This brand new 3600 sqft luxury condo, consisting of 5 bedrooms and 5 1/2 baths, is situated directly across from Windham Mountain. Private bathrooms for each bedroom. Large living space built for large groups with refined palates. Skiing and the adventure park are within walking distance. Close to mountain biking and hiking, and 1mi from golf at Windham Country Club. 1,000 sq ft of private decks to take in mountain mornings and unwind with a latte. Managed by Cedar Properties.

The Mad Brook House | Walk to Main St, Windham

Walk to Main Street from this cozy Catskills cottage by the brook! The Mad Brook House is a newly refreshed two-bedroom, one-bath retreat in the heart of Windham — perfect for couples, small families, or friends visiting the mountains. Dating back to 1940, the home has been beautifully updated to combine classic Catskills character with modern comfort. Relax beside the gentle brook just steps from your door, or stroll to Main Street for dining, shopping, and coffee!