Vacation 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.

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.

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.

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!

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.

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!

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!

Mountain-Modern 5BR Home • Windham & Hunter • EV

A 5 bedroom , spacious, 5-acre mountain modern home boasting all comforts and amenities you could need in the heart of the Catskills! The house is tucked away, secluded, meanwhile just minutes away from lakes, hike trails, golfing, ATV rentals, breweries, farmers markets, restaurants, vineyards, local shops and skiing or snowboarding at either Windham Mountain resort or Hunter Mountain! Welcome to GreeneHaus!