
House vacation rentals in Windham
Find and book unique houses on Airbnb
Top-rated house rentals in Windham
Guests agree: these houses are highly rated for location, cleanliness, and more.

Embrace winter in style at #killercatmountainhouse
Listed by Rolling Stone Magazine as a “Best Airbnb for large groups in North America,” #killercatmountainhouse is an ultra-private retreat at Hunter Mt where natural splendor meets seductive style. Our Parisian-chic décor with fireplace, expansive deck, game room & custom kitchen gives design lovers Insta-worthy moments inside & out, while our epic views & amenities—including a hot-barrel sauna, firepit, roomy hot tub & Tesla EV charger—allow outdoor & eco enthusiasts to indulge all winter long.

Catskills Retreat: Hot Tub | Fireplace | Firepit
Year-Round Catskills Retreat Escape to Five Star Cottage in Windham, NY, just 2 hours from NYC. This spacious 4-bedroom, 2.5-bath home features stunning mountain views, a cozy wood-burning fireplace, a hot tub, and a large deck for year-round enjoyment. Ski in the winter, and explore nearby hiking trails, lakes, and waterfalls in the warmer months. Ideal for families and groups seeking adventure, wellness, or a peaceful retreat. Book your stay today and experience the beauty of the Catskills!

Cheerful Catskill Village Cottage
Bright and airy Catskill village refuge - a wildflower and wildlife haven in the thick of things. Historic house set on a quarter acre of trees and wildflowers, but blocks from Main Street, Catskill. Walk to Foreland, The Lumberyard, the incredible village cemetery, Thomas Cole House, restaurants and shops. Olana State Historic Site is right across the bridge! Cottage has a full kitchen, clawfoot tub, penny tile shower, front porch, dining room and large living room. Truly peaceful and lovely.

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 :)

Hunter Mtn Ski Chalet! Hot Tub, Outdoor TV Firepit
Located 10 minutes to Hunter Mountain & 20 minutes to Windham & Belleayre Mountains. This newly-remodeled, former schoolhouse is the perfect getaway! Home sits right on Stony Clove Creek & features an outdoor tv & hot tub, creekside fire pit with egg chairs, cozy fireplace inside, thoughtful amenities, outdoor games, board games & picturesque mountain views! Enjoy private access to the creek! The home is located along Stony Clove Creek & is minutes to Phoenicia, Hunter & Tannersville.

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!

Catskills, secluded, a renovated 1840s Barn w/SPA
Welcome to PostBeamLove. An idyllic private secluded 4-season dream 10-acre getaway. Stay and indulge in complete comfort in a fully converted 1840s Dairy Barn with indoor saltwater hot tub & sauna with mountain views, overlooking the northwestern Catskills in the heart of Roxbury. The property features a spring-fed pond, gazebo, stream, & a neighboring farm. A 10-min drive to Plattekill Mtn, one of the best-kept secrets for avid skiers. Or go hiking, have a picnic, even golf.

Chalet with HotTub 5 min to Windham, 15 min Hunter
Cozy Chalet style house nestled in a quiet spot and 5 minutes to Windham Mountain and close to hiking trails 15 minutes to Hunter Mountain 40 minutes to Belleayre Mountain. Relax by the fireplace after skiing TV with Netflix, Amazon and Hulu. Confortable couch with a equipped kitchen With 3 bedrooms. This property has a beautiful yard. Fairly private yet close to everything. Supermarket and restaurants near by (5 min by car) 15 min. to Colgate Lake 25 min. to Kaaterskill Falls

Modern Prefabricated Architectural Retreat
At Stonewall Hill, a modern prefab home set on 10 wooded acres, you can enjoy a cozy night by the fire in winter & cook a feast in the well-equipped kitchen or on the outdoor gas grill in summer. It has an open plan kitchen, living & dining space; a main bedroom w/ queen bed & ensuite bathroom; a 2nd bedroom that doubles as TV room w/ queen sofa bed & bathroom across the hall. 10 minutes to the HITS fairgrounds & close to hiking, skiing, shopping, & dining.

Lux Modern Cabin at Hunter Mountain
Modern private retreat in the heart of the Catskills with expansive views of Hunter Mountain that delivers an ultra-lux getaway experience. Casa Nevana is a brand-new construction. Enjoy each season of the Catskills in comfort and style. Immerse yourself in nature and slow living while experiencing luxurious accommodations and impeccable design. Follow us on IG @CasaNevana to see more of the home, local hot spots and more!

Modern Ski-Home With Views Near Hunter & Windham
Our home is a modern, relaxing space to decompress, explore, and take time to breathe in the fresh mountain air. Tailor-made for relaxation, family-time, and endless outdoor activities. Stoke a roaring fire indoors or outdoors in a beautiful fire pit for those cooler summer and fall nights. Close proximity to hiking and sunbathing at the lake in the summer and skiing in the winter.

Modern Mountain Retreat with Views on 18 Acres
Relax and find your bliss in this modern stylish retreat on eighteen private acres. Landola Lodge has been recently renovated into a spa-like space that includes cozy beds, luxurious walk-in shower and soaking tub, entertainment lounge with Roku TV, High-Speed Internet, gas fireplace, central AC/Heat, washer/dryer, dishwasher, beautiful mountain views, deck, outdoor grill, and fire pit.
Popular amenities for Windham house rentals
House rentals with a pool

Spacious Winter Retreat Near Woodstock Village

Catskills SKI HAUS Winter Wonderland

Bluestone Escape - Where everyone is at home.

Gorgeous Villa MntnViews, nr SKI, firepl, hot tub!

Hawk View

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

Upstate Modern Scandinavian Barn in the Catskills

Warm & Comfortable Family Stay nr Woodstock
Weekly house rentals

The Mad Brook House | Walk to Main St, Windham

Hot tub with stunning views, 5 min to Woodstock

Hot Tub, Sauna & Fire Pit. 10 min to ski

Athens, NY House - 1 Bedroom "Want to Get Away"?

Mt. Wonder: Cozy Cabin w/ Hot Tub and Wow View

Mountain Magic awaits you!

Catskill Clubhouse

Great for hunters-skiers-hikers close to Windham
Private house rentals

Hyttå|Cozy Nordic Retreat|Hot Tub|Clubhouse|Wifi

Sunswick Railcar: A 1940s Train Among the Trees

Excellent Comfort and Location

Walk to town | 2 Mins to Ski | Windham Mill House

Peaceful Woods at The Johnson Cottage

Cozy Alpine Condo 4-Min to Ski

Catskill Mountains Forest Nest for 2

Charming Catskills Cottage
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,715 | ﺩ.ﺇ1,913 | ﺩ.ﺇ1,675 | ﺩ.ﺇ1,469 | ﺩ.ﺇ1,465 | ﺩ.ﺇ1,381 | ﺩ.ﺇ1,362 | ﺩ.ﺇ1,414 | ﺩ.ﺇ1,465 | ﺩ.ﺇ1,465 | ﺩ.ﺇ1,528 | ﺩ.ﺇ1,568 |
| Avg. temp | -4°C | -3°C | 2°C | 9°C | 15°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | -1°C |
Quick stats about house rentals in Windham

Total vacation rentals
Explore 80 vacation rentals in Windham

Nightly prices starting at
Windham vacation rentals start at ﺩ.ﺇ514 per night before taxes and fees

Verified guest reviews
Over 2,450 verified reviews to help you choose

Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
80 of Windham vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Windham rentals

4.9 Average rating
Windham stays are highly rated by guests—averaging 4.9 out of 5!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Windham Mountain
- Resorts World Catskills
- Catamount Mountain Ski Resort
- John Boyd Thacher State Park
- Howe Caverns
- Glimmerglass State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Butternut Ski Area and Tubing Center
- Plattekill Mountain
- Zoom Flume
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Walkway Over the Hudson State Historic Park
- June Farms




