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 $120 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.

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Guest favorite
Home in Durham
4.95 out of 5 average rating, 145 reviews

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

Top guest favorite
The exterior of a charming A-frame house is depicted under a dusk sky, adorned with warm lights that outline the roof. A welcome sign is displayed beside a green front door, which is enhanced by a decorative wreath. Soft landscaping and pathway lighting create a cozy ambiance.
Home in Windham
5.0 out of 5 average rating, 414 reviews

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 :)

Guest favorite
A charming covered front porch features two rocking chairs and is framed by vibrant orange marigolds and lush greenery. An American flag gently waves nearby, adding to the welcoming atmosphere of the home.
Home in Durham
4.89 out of 5 average rating, 107 reviews

Idyllic Mountain view Catskills home near Windham

Nestled in the mountain, this beautiful three bedroom home has character galore, from the covered front porch to the birch log handrails leading to the loft. The views are bucolic; out the back is the Catskill Mountain range, and out the front is the Helderbergs. This is a very desirable location, only 15 minutes from Ski Windham. There are cathedral ceilings in the living room and dining room, and exposed beams in the large kitchen. The skylights and large windows bring the outside in.

Top guest favorite
A modern cabin design features broad wooden slats and floor-to-ceiling glass doors. A spacious deck includes loungers and a hot tub, surrounded by lush greenery, enhancing the outdoor aesthetic. Soft lighting illuminates the seating area, creating a welcoming environment.
Home in Hunter
4.96 out of 5 average rating, 224 reviews

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!

Top guest favorite
An above ground pool is situated in a spacious yard surrounded by lush greenery. The pool's clear blue water reflects the sky, while a nearby patio area is equipped with seating and umbrellas. A charming red house serves as a backdrop, completing the serene outdoor scene.
Home in Windham
4.95 out of 5 average rating, 106 reviews

Private Estate | 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.

Guest favorite
A single-story home is set amidst lush greenery, featuring a wooden deck with a roof and a ramp leading to its entrance. Well-maintained flower beds surround the entrance, while a spacious lawn extends into the background.
Home in Jewett
4.9 out of 5 average rating, 105 reviews

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.

Superhost
An open living area showcases a wooden ceiling with beams and a rustic dining table surrounded by black chairs. A cozy couch faces a brick fireplace, while a modern kitchen with stainless steel appliances is visible in the background. Soft lighting from a chandelier adds warmth to the space.
Home in Windham
4.79 out of 5 average rating, 133 reviews

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

Top guest favorite
Home in Prattsville
4.97 out of 5 average rating, 104 reviews

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!

Top guest favorite
Home in East Jewett
4.99 out of 5 average rating, 144 reviews

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.

Top guest favorite
An open-concept living area features a deep leather couch and two comfortable chairs, with large sliding glass doors offering expansive views of the autumn foliage and mountains. A round wooden coffee table complements the space, which is accented by a textured light fixture and a dining table in the background.
Home in Hunter
4.99 out of 5 average rating, 156 reviews

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!

Guest favorite
The image displays a charming red house with two stories, featuring a welcoming front porch with white railings. A snow-covered yard surrounds the home, while a large tree is positioned to the left. The clear blue sky adds to the serene atmosphere.
Home in Windham
4.91 out of 5 average rating, 141 reviews

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.

Guest favorite
An inviting fire pit area is surrounded by six green Adirondack chairs arranged in a circle, set on a stone path of gray gravel. In the background, a multi-level deck extends from the house, surrounded by trees in a serene outdoor setting.
Home in Hensonville
4.93 out of 5 average rating, 107 reviews

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

When is the best time to visit Windham?

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