
House holiday rentals in Windham
Find and book unique houses on Airbnb
Quick stats about house rentals in Windham

Total holiday rentals
Explore 90 holiday rentals in Windham

Nightly prices starting at
Windham holiday rentals start at €104 per night before taxes and fees

Verified guest reviews
Over 2,570 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
80 of Windham holiday rentals include wifi 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!
Top-rated house rentals in Windham
Guests agree: these houses are highly rated for location, cleanliness and more.

Wow! Panoramic Mountain View, Minutes to Windham!
This pristinely-kept vacation home has endless mountain views on rolling country acres. Come and stay just to get away, enjoy both the sunrise and sunset views from the expansive deck. Curl up by the wood burning fireplace or the outdoor fire-pit, or take a sunset plunge in our backyard hottub and enjoy the picturesque views of Windham, NY from across the valley. A serene 8 mile drive will take you into the historic Town of Windham, NY to enjoy a day of skiing, site-seeing, hiking or dining

Spacecraft Sanctuary x Stargate Self-Care Retreat
Nestled into a private forested locus in the charming hamlet of Halcottsville, NY is SPACECRAFTX1 SANCTUARY, a transformed single wide trailer with walls of glass sliders that showcase the ultimate designer, Mother Nature with her majestic mountain vistas, perennial x calming Japanese rock gardens. SPACECRAFTX1 STARGATE (separate structure) is a wellness studio for yoga, pilates, barre x meditation with an infrared sauna with chromotherapy for a “Design Your Own” self-care retreat experience.

Scandi A-Frame w/Hot Tub & Sauna
Escape to Wilderkaat {WILL-der-cat} ⮕ NEW GUT RENO 3-bed 2-bath Scandinavian modern A-frame chalet ⮕ 2 private wooded acres ~10 miles to Hunter & Windham ⮕ 8-person hot tub, cold plunge tub, 6-person barrel sauna ⮕ Backyard firepit w/Adirondack chairs & string lights ⮕ Outdoor games: bocce cornhole horseshoes disc golf ⮕ Fully stocked open kitchen, Weber grill, in & outdoor dining for 8 ⮕ Smart TVs & Sonos throughout, high-speed fiber WiFi ⮕ A Catskills perfect blend of relaxation & adventure

Private Waterfall Retreat on 10 acres
Newly renovated 2 BR private home in the Catskill foothills perched next to a beautiful waterfall and stream. Furnished with quality and care, with an eye toward modern style and comfort. Gas Grill on covered porch, Campfire area, & outdoor table and benches for dining outside! Hiking trails and swimming holes nearby. Walking distance to Zoom Flume Waterpark, 12 mile drive to Windham Mountain, 30 minutes to Hudson. But really no need to go anywhere once you settle in to this quiet retreat!

Private cabin in the Catskills
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 :)

Valley View Chalet: AC, Hot Tub, Firepit, Games
Spacious, peaceful lux cabin atop the Catskills. Enjoy mountain views and soak in the hot tub. Catch up in the vaulted room by the stone fireplace w/ a wide game selection, with a 2nd living room downstairs. Host a dinner party with our fully equipped kitchen. 20 mins to 6 towns. Visit breweries, antique shops, dine, hike, fish, golf, or relax. Great for groups, families, kids & pets. Fast 600mb internet, AC, EV charger, generator. WFH, newborn, pet friendly. 3+ nights get discounted rate

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!

Mountain Chalet Retreat New Hot Tub
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

Catskills Retreat - Game Room, Hot Tub, EV charger
Welcome to our Mountain Chalet. Bring the whole family to this spacious retreat with plenty of room for fun and relaxation.This specious house, nestled on 2.5 acres, features 4 bedrooms, 3 full bathrooms, Hot Spring hot tub, a game room, a cozy gas fireplace, smart TVs, an EV charger and more. It has beautiful views. Located in the heart of the Catskills, 15 min from Windham Mountain, 20-25 min from Hunter and 40 min from Belleayre. Your perfect mountain getaway awaits!

Big Red Retreat 3 min to Windham Mountain & Golf!
Welcome to Big Red – Your Ultimate Mountain Retreat! Nestled in the heart of the scenic Windham area, Big Red invites you to experience the perfect blend of comfort, convenience, and adventure. Whether you're here to hit the slopes at Windham Mountain, explore the tranquil Windham Path, or tee off at the nearby golf course, our spacious 6-bedroom, 2.5-bath home is your ideal basecamp for an unforgettable getaway.

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 house rentals in Windham
House rentals with a pool

Lake House close to Skiing & Indoor Hot Tub

Private Estate | 6BDRM, Pool, Hot Tub & Movie Room

Woodstock Family Home w/ Tree House + Heated Pool
Woodstock Historic Artist Estate - The Pond House

Gorgeous Villa Mntn Views • POOL • hot tub •grill!

Highwoods Haven | saltwater pool and hot tub

Hudson River Sunset Getaway

Hudson Valley Lake · Hot Tub · Dock · Games · View
Weekly house rentals

EAT, DRINK, PLAY ... and Relax in Windham

Idyllic Mountain view Catskills home near Windham

Pawfect Family Retreat w/fenced-in yard & Dog Park

Modern Luxury Mountain View Retreat + Hot Tub

Europe in The Catskills

Catskills Mountaintop House w/ HOT TUB and VIEWS!

Peaceful Woods at The Johnson Cottage

The Mad Brook House | Walk to Main St, Windham
Private house rentals

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

Excellent Comfort and Location

Catskill Mountains Cabin

Ski Hunter Mountain w/ Views | Fire Pit | 5 Acres

Cozy stylish Cabin in the Woods

Blackwood Retreat • Hot Tub, Sauna & Fire Pit

The Jewett house

Luxury Retreat-Heated Pool, Sauna, HotTub&C Plunge
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €431 | €412 | €346 | €368 | €343 | €352 | €321 | €333 | €346 | €324 | €349 | €432 |
| 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 |
Destinations to explore
- New York City Holiday rentals
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- Cabin rentals Windham
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- Pet-friendly rentals Windham
- Townhouse rentals Windham
- Family-friendly rentals Windham
- Rentals with pools Windham
- Chalet rentals Windham
- Ski-in/ski-out rentals Windham
- Rentals with a hot tub Windham
- House rentals Greene County
- House rentals New York
- House rentals United States
- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Resorts World Catskills
- Windham Mountain
- June Farms
- Catamount Mountain Ski Resort
- Howe Caverns
- Glimmerglass State Park
- Butternut Ski Area and Tubing Center
- Plattekill Mountain
- Taconic State Park
- Thacher State Park
- Mohonk Preserve
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Peekamoose Blue Hole
- Millbrook Vineyards & Winery
- Rensselaer Polytechnic Institute
- Hudson Chatham Winery
- MVP Arena
- Naumkeag
- Lake Minnewaska
- New York State Museum





