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

Total vacation rentals
Explore 90 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 2,570 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!
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

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 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!

Lux Hunter Mountain Retreat | Sauna + Game Room
NEW ♨️ Private Sauna + Family Game Room! Escape to our beautifully remodeled 3BR/2BA mountain retreat set on 6 private acres in Jewett. Relax in your private indoor sauna or enjoy the game room with arcade, foosball, and darts. 📍 ~10 minutes to Hunter & Windham Mountains 📍 ~2.5 hours from NYC — an easy year-round getaway Ski, hike, bike, swim, golf, fish, explore local vineyards, or dine out — all within 10 minutes. Then return to comfort, space, and peaceful mountain surroundings.

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!

Luxury Retreat | 6BDRM, Pool, Hot Tub & Movie Room
A private six-bedroom estate offering refined comfort and luxury. Nestled within the Dingley Dell Estate, it's just a six-minute drive to Windham town and about 25 minutes from Hunter Ski Resort. The property features expansive, beautifully landscaped grounds, inviting outdoor seating areas, a prime location, and exceptional privacy. Completely renovated for maximum guest comfort, the home also includes a pool, movie room, premium sound system, and breathtaking mountain surroundings.

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!

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.

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!
Popular amenities for Windham house rentals
House rentals with a hot tub

Greenville Getaway|Paws & Pines: Dog Park & HotTub

Embrace nature in style @ #killercatmountainhouse

Windham Farmhouse Escape

Mt. Wonder: Big Cozy Cabin with Wow View

Charming Home Lg/Mod Kit Hot Tub on Stream FirePit

Secluded 55 acre Windham Getaway w/ 6BRs + Hot Tub

Catskills Mountaintop House w/ HOT TUB and VIEWS!

Cozy Mountain Cottage with Pond & Hot Tub
House rentals with a pool

Hudson River Sunset Getaway

Charming home - views of Hunter Mountain slopes
Woodstock Historic Artist Estate - The Pond House

Upstate Getaway btw Rhinebeck+Hudson

Hudson Valley Lake · Hot Tub · Dock · Games · View

Hawk View

Highwoods Haven | saltwater pool and hot tub

Hudson River estate guest cottage
Family-friendly house rentals

Big Red Retreat 3 min to Windham Mountain & Golf!

Pet Friendly, Close to Hiking and Mountain Lakes

Lux Modern Cabin at Hunter Mountain

Architectural wonder in the woods

Modern Forest Retreat with Hot Tub and Sauna

The Mad Brook House | Walk to Main St, Windham

Europe in The Catskills

EAT, DRINK, PLAY ... and Relax in Windham
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 1,561 | ﺩ.ﺇ 1,454 | ﺩ.ﺇ 1,495 | 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 |
Destinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Boston Vacation rentals
- Ocean City Vacation rentals
- Niagara Falls Vacation rentals
- Portland Vacation rentals
- Jersey City Vacation rentals
- Mississauga Vacation rentals
- Baltimore Vacation rentals
- Newark Vacation rentals
- Cabin rentals Windham
- Cottage rentals Windham
- Condo rentals Windham
- 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
- June Farms
- Windham Mountain
- Catamount Mountain Ski Resort
- Howe Caverns
- Glimmerglass State Park
- Butternut Ski Area and Tubing Center
- Taconic State Park
- Mohonk Preserve
- Plattekill Mountain
- Thacher State Park
- Bash Bish Falls State Park
- Peekamoose Blue Hole
- Hunter Mountain Resort
- Zoom Flume
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Rensselaer Polytechnic Institute
- MVP Arena
- Lake Minnewaska
- Naumkeag





