
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.

Mt. Wonder: Big Cozy Cabin with Wow View
Welcome to Mt Wonder. With a wood burning hot tub, this secluded cabin sits on 18 acres with creek access, a vast forest & the greatest view in the county. Ten min to Woodstock. Seeking a vacation w friends or a romantic escape? Enjoy this rustic 2br 1ba cabin, cozy and spacious, with a unique magical feel. Mega amenities incl the tub, BBQ, wood stove & stocked kitchen. Peruse our books, vibe w the view, enjoy hikes & cute towns. Need more space? Try my cousin cabin: "Wonders Never Cease"

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

Embrace nature in style @ #killercatmountainhouse
Natural splendor meets seductive style at #killercatmountainhouse, a design-focused retreat 5 minutes from Hunter Mountain—and 13 minutes to Windham Mountain—that delivers a fresh & unexpected Catskills experience. Embrace summer from our expansive deck, hot-barrel sauna, fire pit & roomy hot tub, or unwind by the fireplace w/records & games. Our Parisian-chic décor provides Insta-worthy moments inside & out, while our epic views & amenities allow outdoor enthusiasts to indulge all season long.

Serendipity Lake House on Lake Heloise
Escape to Serendipity — your private lakefront sanctuary in the Catskills, perfect for ski getaways, family retreats, special events, and nature lover's paradise. Unwind in a 4,000 sq ft lodge with cathedral ceilings, a lakeside deck, hot tub, fire pit, boating, and fishing access — all on 9.5 acres of breathtaking scenery. Just minutes from skiing, hiking, and fall foliage drives, this is the ultimate all-season destination. House sleep 14 people with room for more. Over 14 people $60/person.

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 :)

HEAVEN ON EARTH - Hudson Riverfront Home
Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

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!

Pet Friendly, 10 mins to Hunter & Windham mountain
Looking for a private getaway with a gorgeous view? This secluded home is situated on 4.5 acres just a couple of miles from the entrance to Hunter Mountain. There is a beautiful kitchen, a cozy fireplace, a bar, dining room, deck with a stunning view, fire pit and a barbecue grill. Our cleaners follow strict CDC and Airbnb guidelines. All surfaces are cleaned and sanitized before your arrival. Surrounded by hiking, biking, lakes to enjoy and skiing in the winter! Come and enjoy!

Sweet cottage near Hunter Mountain
This is our home away from home where we love to go in our free time. The house is 10 min drive from Hunter mountain or Windham. Great for skiing in winter / hiking in summer. WiFi: YES! High speed internet, Fiber Optic, 200Mbps. Perfect for work from home. Netflix, Disney+ and great selection of movies is available for all guests which you may enjoy on new 75 inch TV. Great for movie nights! Sound system through out the house is also available. Baby equipment upon request.

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

Great for hunters-skiers-hikers close to Windham
The quiet tranquility of mountain nature. Minutes from the Windham mountain ski resort. State land nearby for hunters as well. This one bedroom home has key pad entry, a full kitchen, dining area, living room, front deck, spacious rear deck, fire pit, acres of back yard, full bathroom, can sleep four with queen size bed and pull out couch, wifi, fire stick tv. All the comforts of home. This is a fully furnished one bedroom home that was recently converted to an Air BNB.
Popular amenities for Windham house rentals
House rentals with a pool

Lake House close to Skiing & Indoor Hot Tub

Heated Pool • Private • 4 Min to Woodstock

Shaggerties Cozy Catskills Getaway

Highwoods Haven | saltwater pool and hot tub

Hudson River Sunset Getaway

Hawk View

MODERN FARMHOUSE in the WOODS

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis
Weekly house rentals

Catskills Retreat - Game Room, Hot Tub, EV charger

Europe in The Catskills

Peaceful Woods at The Johnson Cottage

The Elsbree House - Summer Destination

Lux Windham Getaway | Views & Indoor Heated Pool

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

Lux Farmhouse - Hot-tub/Sauna/Firepit/Game Room

Book Village Inn - Dickinson Room Queen Bed
Private house rentals

Excellent Comfort and Location

Windham Chalet with Treehouse, sleeps 15

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

Arcade|Music|BBQ|Fire Pit|Acres|Batavia House!

Catskill Mountains Cabin

Lux Hunter Mountain Retreat | Sauna + Game Room

Catskills Cabin Escape with Hot Tub

Peaceful streamside in nature near skiing & hike
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,829 | ﺩ.ﺇ 1,748 | ﺩ.ﺇ 1,469 | ﺩ.ﺇ 1,469 | ﺩ.ﺇ 1,465 | ﺩ.ﺇ 1,381 | ﺩ.ﺇ 1,362 | ﺩ.ﺇ 1,414 | ﺩ.ﺇ 1,465 | ﺩ.ﺇ 1,374 | ﺩ.ﺇ 1,480 | ﺩ.ﺇ 1,833 |
| 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.ﺇ 441 per night before taxes and fees

Verified guest reviews
Over 2,590 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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- House rentals Greene County
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Resorts World Catskills
- Howe Caverns
- Glimmerglass State Park
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Plattekill Mountain
- Windham Mountain
- Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Taconic State Park
- Hunter Mountain Resort
- June Farms
- Walkway Over the Hudson State Historic Park
- Millbrook Vineyards & Winery
- Naumkeag
- Poets' Walk Park
- Hudson Chatham Winery
- Norman Rockwell Museum
- Opus 40
- New York State Museum





