
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

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 :)

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!

Rustic Swedish Barn/Featured in Airbnb Magazine
Enjoy expansive views of the Catskill Mountains from this renovated but rustic Scandinavian barn. Featured in many magazines and catalogues, including AirBnB Magazine. Walk the property, with its big open field, an organic orchard, walking paths, and flower gardens. A large private pond is swimmable (after heavy rains it does get muddy). The Barn has central heat and air conditioning. A full bathroom features an antique bathtub. Enjoy dining inside, or outdoor grilling and dining.

Catskills Mountaintop House w/ HOT TUB and VIEWS!
Welcome to the best sweeping views in all of the Catskills! This secluded getaway sits on more than 8 acres of land without a neighbor in sight! Whether you are looking to vacation with friends and family, or a romantic escape, this is the place for you. Enjoy this 3 BD 2.5 BA home year round, including our 8 person hot tub! Amenities galore including outdoor firepit, lounge chairs, sledding, BBQ, ping pong, board games, TV and more. This house is perfect for travelers of all types!

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.

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!

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.
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 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

Catskill Village Ski Hike Lake Pet Main St Pool
Weekly house rentals

Idyllic Mountain view Catskills home near Windham

Scandinavian Cottage/Mountain Views/Fire pit

The Mad Brook House | Walk to Main St, Windham

Cozy Mountain Cottage with Pond & Hot Tub

Lux Hunter Mountain Retreat | Sauna + Game Room

Pet Friendly, Close to Hiking and Mountain Lakes

Hot tub with stunning views, 5 min to Woodstock

Private Waterfall Retreat on 10 acres
Private house rentals

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

Excellent Comfort and Location

Modern Luxury Mountain View Retreat + Hot Tub

Lux Mountain Retreat w/ Heated Indoor Pool

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

Cozy stylish Cabin in the Woods

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 | €432 | €413 | €347 | €368 | €343 | €353 | €322 | €334 | €346 | €324 | €349 | €433 |
| 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
- June Farms
- Windham Mountain
- Catamount Mountain Ski Resort
- Howe Caverns
- Glimmerglass State Park
- Butternut Ski Area and Tubing Center
- Mohonk Preserve
- Taconic State Park
- Plattekill Mountain
- Thacher State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Peekamoose Blue Hole
- Zoom Flume
- Millbrook Vineyards & Winery
- Rensselaer Polytechnic Institute
- Hudson Chatham Winery
- MVP Arena
- Lake Minnewaska
- Naumkeag





