House holiday rentals in Windham

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Top-rated house rentals in Windham

Guests agree: These houses are highly rated for location, cleanliness and more.

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Guest favourite
A cozy living room features a stone fireplace as the focal point, complemented by large windows that offer views of the outdoor deck. A wooden coffee table is surrounded by wicker chairs, and a decorative plant adds a touch of greenery.
Home in Windham
4.89 out of 5 average rating, 140 reviews

Catskills Retreat: Hot Tub | Fireplace | Firepit

Year-Round Catskills Retreat Escape to Five Star Cottage in Windham, NY, just 2 hours from NYC. This spacious 4-bedroom, 2.5-bath home features stunning mountain views, a cozy wood-burning fireplace, a hot tub, and a large deck for year-round enjoyment. Ski in the winter, and explore nearby hiking trails, lakes, and waterfalls in the warmer months. Ideal for families and groups seeking adventure, wellness, or a peaceful retreat. Book your stay today and experience the beauty of the Catskills!

Top Guest favourite
A cozy living room features floral-patterned armchairs and a sofa, complemented by a low coffee table. A lamp provides soft lighting, and artwork hangs on the walls, enhancing the warm decor. A textured rug covers the floor, adding comfort to the space.
Home in Catskill
4.97 out of 5 average rating, 190 reviews

Cheerful Catskill Village Cottage

Bright and airy Catskill village refuge - a wildflower and wildlife haven in the thick of things. Historic house set on a quarter acre of trees and wildflowers, but blocks from Main Street, Catskill. Walk to Foreland, The Lumberyard, the incredible village cemetery, Thomas Cole House, restaurants and shops. Olana State Historic Site is right across the bridge! Cottage has a full kitchen, clawfoot tub, penny tile shower, front porch, dining room and large living room. Truly peaceful and lovely.

Top Guest favourite
Home in Durham
4.96 out of 5 average rating, 142 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 favourite
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
4.99 out of 5 average rating, 392 reviews

Custom Catskills private retreat

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 favourite
An outdoor hot tub is situated on a wooden deck, with a 55-inch TV mounted on the wall nearby. Soft lighting creates an inviting ambiance as the sun sets behind distant hills, offering a serene escape for relaxation and entertainment.
Home in Lanesville
4.92 out of 5 average rating, 151 reviews

Hunter Mtn Ski Chalet! Hot Tub, Outdoor TV Firepit

Located 10 minutes to Hunter Mountain & 20 minutes to Windham & Belleayre Mountains. This newly-remodeled, former schoolhouse is the perfect getaway! Home sits right on Stony Clove Creek & features an outdoor tv & hot tub, creekside fire pit with egg chairs, cozy fireplace inside, thoughtful amenities, outdoor games, board games & picturesque mountain views! Enjoy private access to the creek! The home is located along Stony Clove Creek & is minutes to Phoenicia, Hunter & Tannersville.

Guest favourite
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
4.95 out of 5 average rating, 192 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 favourite
A modern living room is featured, highlighting large bay windows that provide a view of the surrounding nature. A comfortable leather sofa is paired with a side chair and decorative plants. Wooden doors and light-colored walls enhance the spacious feel, complemented by a subtle area rug.
Home in Saugerties
4.98 out of 5 average rating, 103 reviews

Cozy Winter Upstate Cabin

Beautiful 2 bedroom/1 bath home centrally located between Woodstock and Saugerties in the gorgeous Catskill Mountains. Come for hiking, skiing, shopping and dining, it is all at your fingertips! Your home is a chic cabin situated on a large property and provides a fully stocked kitchen if you choose to cook at home, a gas grill, and fire pit in the back yard for evening enjoyment. Visit the many fun shops just down the road, or one of our lovely locally owned restaurants! Enjoy!

Guest favourite
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
4.83 out of 5 average rating, 115 reviews

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

Top Guest favourite
An inviting outdoor space features four Adirondack chairs arranged around a circular firepit. The background showcases a two-story chalet with large windows and a balcony. Lush greenery and mountain views are visible, creating a peaceful atmosphere, especially during sunset.
Home in Hunter
4.99 out of 5 average rating, 131 reviews

Private Chalet with Mountain Views

The Hunter Mountain House is a 4-bedroom, 2-bath, secluded 3 .5 acre retreat minutes from the slopes, hiking, shopping, and great food. Enjoy this peaceful property with beautiful mountain views. Enjoy hotel-style amenities to enhance your getaway. Throw on one of the fluffy white robes, brew a mug from the fully stocked coffee/tea bar, play some vintage records by the fireplace and soak in the outdoor hot tub. Brought to you by Mountain House Collective.

Top Guest favourite
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
4.98 out of 5 average rating, 129 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 favourite
An open living space features a modern design with skylights and large windows providing natural light. A stone fireplace is situated near the seating area, which is complemented by a dining table and chairs. Warm wooden flooring adds to the inviting ambiance.
Home in East Jewett
4.97 out of 5 average rating, 263 reviews

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.

Top Guest favourite
Home in Halcott
4.98 out of 5 average rating, 130 reviews

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 Windham house rentals

When is the best time to visit Windham?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$691 AUD$771 AUD$675 AUD$592 AUD$591 AUD$557 AUD$549 AUD$570 AUD$591 AUD$591 AUD$616 AUD$632 AUD
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Quick stats about house rentals in Windham

  • Total holiday rentals

    Explore 80 holiday rentals in Windham

  • Nightly prices starting at

    Windham holiday rentals start at $133 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Windham holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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