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House vacation 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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Top guest favorite

A cozy outdoor space features comfortable seating and a modern fireplace, set against a stunning backdrop of lush trees and a colorful sunset. A hot tub is visible nearby, inviting relaxation. Soft lighting adds a warm touch to the tranquil atmosphere.

Home in Lexington

4.99 out of 5 average rating, 116 reviews

Mountain View Chalet: AC, Hot Tub, Firepit, Games

Spacious, peaceful lux cabin atop the Catskills. Enjoy mountain views, make smores, & soak in the hot tub. Catch up in the vaulted room by the fireplace w/ our wide game selection, while others watch movies downstairs. Host a dinner party with our fully equipped kitchen. Centrally located, 20 mins to 6 towns. Visit breweries, antique shops, dine, hike, fish, golf, or relax. Fast 600mbps internet. Perfect for groups, families, kids & pets. WFH, newborn, pet friendly. 3+ nights get discounted rate

Top guest favorite

Home in Roxbury

5 out of 5 average rating, 162 reviews

Private 3BR escape w/ sweeping Mt Views & Firepit!

Click: "Show more" to read description before booking. NO PETS Perched high on a private road, The Ridge is a 3 BR / 2 bath newly constructed modern farmhouse w/ sweeping mountain views. Relax & dine outdoors on the wrap around deck & discover all of the comforts of home inside the open concept living space. Set on 5 mountainside acres, 3 min to Roxbury town & 10 min to wedding venues. Outdoor adventures await- 4 season activities at ski mountains, hiking, golf, farmers markets & culinary tours

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

4.88 out of 5 average rating, 136 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!

A single-story house is set against a backdrop of rolling hills with autumn foliage. A wide deck with white railings provides access to the entrance. The expansive lawn features well-maintained grass and a clear blue sky overhead.

Home in Prattsville

4.91 out of 5 average rating, 315 reviews

Yanity House

You will have access to the entire house fully furnished. Pet's are welcome just keep paws clean its a beige rug. We want everyone to be comfortable, so please let us know how and what you would like to see improved if you rent the unit. We will improve the unit as per guest suggestions. Currently we do not have cable but we do have a dvd and game system in the living room - All the bedrooms have TV's, dvd players or bring your streaming device There currently is no phone but cell service works

A peaceful outdoor setting features several white Adirondack chairs arranged around a campfire-style fire pit. Lush green grass and trees frame the scene, while distant mountains and a blue sky with clouds create a serene backdrop.

4.95 out of 5 average rating, 133 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

A modern kitchen features natural wood cabinetry and shelves adorned with an array of dishes and glassware. A window above the sink offers a view of the outdoors, while warm wood paneling accentuates the ceiling.

Home in Cornwallville

4.98 out of 5 average rating, 150 reviews

Private Waterfall Retreat on 10 acres

Newly renovated 2 BR private home in the Catskill foothills perched next to a beautiful waterfall and stream. Furnished with quality and care, with an eye toward modern style and comfort. Gas Grill on covered porch, Campfire area, & outdoor table and benches for dining outside! Hiking trails and swimming holes nearby. Walking distance to Zoom Flume Waterpark, 12 mile drive to Windham Mountain, 30 minutes to Hudson. But really no need to go anywhere once you settle in to this quiet retreat!

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

4.99 out of 5 average rating, 366 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 :)

Top guest favorite

A striking mountain retreat is framed by snow-covered landscaping and wooden railings. The entrance features a stone facade and a charming balcony, with the warm wooden roofline extending above. Tall trees provide a natural backdrop, creating a serene winter scene.

Home in Windham

4.94 out of 5 average rating, 101 reviews

Stay on Windham Mt- Mins to Main St + Hot Tub

A unique blend of architectural and design features, this home is one of a kind and perfect for your mountain getaway. The expansive 3800+ sq ft mountain retreat features 5 bedrooms, 5.5 bathrooms, and two large living areas, providing plenty of space to accommodate family & friends. There is also a brand new speakeasy bar to enjoy. Steps to the ski trail (or mountain biking) and hiking, golf, restaurants, and wedding venues, the location is ideal for all seasons. @AlpineLookout on IG

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.

4.95 out of 5 average rating, 152 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!

A single-story home is set among trees, featuring a front porch with a wooden railing. A gravel driveway leads to the entrance, framed by a landscaped area. The surroundings include additional structures and a green landscape, providing a peaceful natural setting.

4.84 out of 5 average rating, 135 reviews

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.

Top guest favorite

4.98 out of 5 average rating, 115 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!

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

4.98 out of 5 average rating, 241 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.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations and amenities

Popular amenities for Windham house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A clear, tranquil swim pond is surrounded by a natural stone border, reflecting the trees and blue sky above. A small, elevated treehouse is visible in the background, adding charm to the serene setting. Warm string lights are hung overhead, enhancing the peaceful environment.

Home in Saugerties

4.88 out of 5 average rating, 132 reviews

Shaggerties - fun cozy catskill mountain getaway

A stock tank plunge pool is surrounded by a wooden deck and gravel, featuring a pink flamingo float. A lounge chair rests nearby, inviting relaxation in the natural setting of greenery.

4.96 out of 5 average rating, 158 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4.88 out of 5 average rating, 147 reviews

4Br Mountain Brook House on 130 acres w/ trails

A serene heated saltwater pool is framed by lush greenery, reflecting the sky above. A rustic wooden edge provides a natural transition between the pool and the surrounding landscape, which includes a prominent tree adding to the tranquil ambiance.

Home in Woodstock

4.92 out of 5 average rating, 245 reviews

Little owl Japanese teahouse: pool is OPEN

A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.

4.88 out of 5 average rating, 319 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Top guest favorite

A spacious deck features two comfortable chairs and a round table at its center, offering a clear view of the expansive Catskill Mountain landscape. Lush greenery and rolling hills stretch into the distance under a bright blue sky.

Home in Stamford

4.98 out of 5 average rating, 116 reviews

Hawk View

An open living space features a grand piano positioned near large windows that offer views of the surrounding mountains. A light-colored sectional sofa and a round coffee table create a comfortable seating area, accented by a dining table beside it. Natural wood beams add architectural interest.

Home in Saugerties

5 out of 5 average rating, 153 reviews

Upstate Modern Scandinavian Barn in the Catskills

A modern living area features large glass doors overlooking a lush green landscape. Natural light fills the space, highlighting the minimalist furnishings, including a stylish sectional sofa and a glass coffee table. Shelving along the wall displays books and decorative items.

Home in Woodstock

4.98 out of 5 average rating, 146 reviews

Woodstock Historic Artist Estate- The Museum House

Weekly house rentals

Top guest favorite

A cozy living area features a wooden ceiling and large windows that allow natural light to brighten the space. Two sofas are arranged around a wooden coffee table, with a television and floor lamp positioned nearby. A colorful area rug adds warmth to the floor.

Home in East Jewett

5 out of 5 average rating, 34 reviews

Mountainside Farmhouse: 2 BR w/ Loft on 4.3 Acres

Top guest favorite

A spacious living area features light wood flooring and large windows allowing natural light. A dining table with chairs is positioned near a cozy wood-burning stove. Sofas include a pullout bed, while decorative elements and bookshelves add warmth to the inviting space.

Home in Prattsville

4.98 out of 5 average rating, 42 reviews

Ashland Cottage—Minutes to Windham Mountain

The inviting living space features a high wooden ceiling, highlighted by a stone fireplace at one end. Two comfortable sofas are arranged around a coffee table, and a large dining area with multiple chairs is visible in the background, creating a cozy gathering spot.

Home in Windham

4.85 out of 5 average rating, 55 reviews

Scenic Mountain Retreat • Hot Tub & Fireplace

The exterior of the house is set amidst a lush forest, featuring a modern black design with large windows. A gently curved driveway leads to a covered entrance, surrounded by trees and landscaped stones.

Home in Windham

4.94 out of 5 average rating, 70 reviews

The Ski Ranch – 5min from Windham Mountain

A spacious main living room features vaulted wooden ceilings and ample natural light from large windows. A stone fireplace is the focal point, while a comfortable seating arrangement includes a sectional sofa and armchairs. A colorful area rug adds warmth to the hardwood floor.

Home in Windham

4.95 out of 5 average rating, 40 reviews

Windham MtView House•2 Mins to Main•Hike & Swim

Top guest favorite

The living area features a spacious open floor plan with cathedral ceilings and a wall of windows allowing natural light. A wood-burning stove is positioned centrally, surrounded by comfortable seating. The decor includes warm wood elements, enhancing the overall inviting ambiance.

Home in Windham

4.93 out of 5 average rating, 56 reviews

Creekside Lodge

Top guest favorite

A spacious living area is presented, featuring a light-colored sectional sofa adorned with throw pillows in varying tones. A wooden coffee table is positioned in front of the sofa, complemented by a simple mug. Large windows allow natural light to illuminate the room, with views of the outdoors.

Home in Tannersville

4.96 out of 5 average rating, 53 reviews

Luxury Retreat Experience Modern Mountain Hideaway

The interior showcases a modern rustic design with wood beams and corrugated metal walls. A cozy seating area features leather furniture, while a queen-sized bed is neatly dressed with linens. Natural light floods through the windows, illuminating a small dining table and a decorative carpet.

Home in East Jewett

4.99 out of 5 average rating, 75 reviews

Catskill Clubhouse

Private house rentals

Top guest favorite

An open living and dining area features high vaulted ceilings and large arched windows, allowing natural light to fill the space. A long dining table with upholstered chairs sits centrally, while a comfortable seating area with a sofa is visible in the background.

Home in Windham

4.94 out of 5 average rating, 53 reviews

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

Top guest favorite

A hot tub is positioned on a wooden deck, with bubbling water visible. In the background, a barn and silos are seen against a clear blue sky. A pond reflects the greenery, with a few chairs placed nearby for relaxation.

Home in Windham

4.98 out of 5 average rating, 96 reviews

Windham Farmhouse Escape

A charming house is set against a backdrop of trees and rolling hills. A wooden deck wraps around the front, featuring steps leading to the entryway. A sun porch is visible to one side, with soft grass and landscaped shrubs complementing the outdoor space.

Home in Prattsville

4.89 out of 5 average rating, 47 reviews

Dog and family friendly home in Lexington, NY!

An open living space features a large leather sectional sofa and a dining table crafted from live edge wood, accommodating ten. Skylights and arched windows allow natural light to fill the room, which is complemented by tasteful artwork and functional bookshelves.

Home in Windham

4.91 out of 5 average rating, 11 reviews

Windham Mountain View Chalet

A view from beneath a wooden gazebo showcases a serene landscape of green grass and evergreen trees. The distant mountains are visible against a bright blue sky, creating a peaceful outdoor setting.

4.95 out of 5 average rating, 81 reviews

6-Acres Lux Oasis with 3BR/2BA - Hunter Mnt Views

Top guest favorite

A charming cottage is nestled among mature trees, surrounded by a lush green lawn. The building features a distinctive orange metal roof and a welcoming front porch. Garden beds are visible in the front yard, contributing to a serene, natural setting.

5 out of 5 average rating, 20 reviews

Charming Catskills Cottage

Two glasses of red wine are placed on a wooden tray, accompanied by decorative nuts. A white vase filled with vibrant orange flowers adds a touch of color to the light-colored countertop.

Home in Hensonville

4.94 out of 5 average rating, 49 reviews

CreeksideHome, 2-5min to Ski,Hiking,Lake,Cafe&Bars

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

4.92 out of 5 average rating, 88 reviews

GreeneHaus - Modern Mountain Escape - EV Charger

Quick stats about house rentals in Windham

Total rentals
80 properties
Nightly prices starting at
R2,501 ZAR before taxes and fees
Total number of reviews
2.5K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

Destinations to explore