Vacation rentals in Windham

4.98 out of 5 average rating, 154 reviews

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

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!

4.98 out of 5 average rating, 250 reviews

The blue cottage is framed by colorful autumn foliage, highlighting shades of red, yellow, and orange. The porch features several chairs and a small table. A grassy area leads up to the cottage, situated on a slight elevation, creating a welcoming outdoor space.

Cabin in Tannersville

Cabin by the woods, Hunter Mountain & Kaaterskills

Our cozy little cottage is tucked away adjacent to the woods. This single floor 650sf apartment is a perfect place to unwind, build a bonfire, & enjoy the nature that surrounds you. Wake up in the morning to watch deer while enjoying your coffee on the porch. Main St. Tannersville is only an 8 min walk; with its nice selection of restaurants & shops. Hunter Mountain & Kaaterskill Falls are within a 10 min drive . Woodstock, Saugertise, Windham, Catskill & Kingston are within a 35 min drive.

4.98 out of 5 average rating, 167 reviews

The log-built chalet is surrounded by lush greenery and rolling hills. A spacious porch wraps around the house, and a fire pit with seating is visible in the foreground, providing a welcoming outdoor space amidst the natural landscape.

Chalet in Gilboa

Secluded Chalet w/ Unforgettable Views on 22 Acres

A nature-lover's oasis, this 3-bedroom/4-bed/2-bath log-built chalet with contemporary furnishings is perched high along the northernmost edge of the Catskill Mountains offering unforgettable panoramic views from inside and out across 22+ secluded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Windam (7 mi), Hunter (16 mi), Catskill (26 mi) and Hudson (29 mi), this is the ideal location from which to explore the best the Catskills has to offer.

4.89 out of 5 average rating, 150 reviews

A cozy bedroom features a spacious bed with a patterned quilt. Bright natural light fills the room through large windows, complemented by soft window treatments. A comfortable chair, wooden dresser, and wall-mounted television add to the inviting space's functionality and warmth.

Townhouse in Windham

Amazing + pet friendly gem in the heart of Windham

Amazing 2 floor spacious getaway with A/C just minutes away from Windham Mountain ski resort, hiking trails, and great restaurants. Family friendly home with a large inviting living room, 2 spacious bedrooms, 2 full bathrooms and wood burning fireplace. Updated kitchen appliances, super-fast Wi-Fi and 3 smart TV's. Many extras including parking, 2 tennis courts, swimming pool and firepit. BBQ Grill on private back deck with scenic views. Winter season rentals preferred during Dec - March.

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.

4.99 out of 5 average rating, 374 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 :)

4.89 out of 5 average rating, 209 reviews

An outdoor pool is surrounded by a spacious deck with multiple lounge chairs positioned for relaxation. Lush greenery forms a serene backdrop, while a set of steps leads into the clear water. A shaded area is visible to the side, enhancing the tranquil setting.

Condo in Windham

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

4.99 out of 5 average rating, 169 reviews

The chalet stands amidst vibrant autumn foliage, showcasing a green exterior and a spacious deck. The well-maintained yard features a lush green lawn, with a variety of trees surrounding the property that enhance the natural setting.

Guesthouse in Windham

Alpine Chalet on Spectacular Property

Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

Superhost

An outdoor seating area is presented alongside a hot tub and a fire pit. The seating features a sectional sofa with light-colored cushions. Dividing panels with a leaf design create a sense of privacy, while surrounding trees provide a natural backdrop.

Cabin in Prattsville

4.89 out of 5 average rating, 261 reviews

Little Red Cabin Near Windham & Hunter w/ Hot Tub

Nestled in the woods, our 3 bedroom cabin offers the perfect escape from the hustle and bustle of everyday life. The cozy interior features a warm, inviting atmosphere with all the amenities you need for a comfortable stay. The spacious living room is the perfect place to unwind after a long day of exploring the great outdoors, complete with a cozy fireplace and outdoor hot tub that offer stunning views of the surrounding landscape. Follow us on IG @thelittleredcabinny

4.95 out of 5 average rating, 144 reviews

The cabin is set in a lush green landscape, surrounded by trees. A spacious deck features outdoor seating, while a fire pit is situated within a circle of chairs, inviting gatherings. The facade displays large windows, enhancing the connection to nature.

Cabin in Windham

The Creekside Cabin - 5 mins to Windham Mt!

Nestled in the hills of Windham NY, the Creekside Cabin is a hidden gem just under 2.5 hours from NYC. Ideal for families and small groups of friends, this cozy cabin features three bedrooms, one bathroom, a comfortable living room overlooking a tranquil creek, and a fully equipped kitchen with a wood-burning fireplace. Whether you're looking for a weekend escape or a longer retreat, the Creekside Cabin offers a peaceful and relaxing stay in a beautiful natural setting.

4.97 out of 5 average rating, 111 reviews

An outdoor deck area features a hot tub surrounded by a wooden railing. Two comfortable chairs and a wooden table provide a relaxing spot to enjoy the scenery. Large windows reflect a serene natural setting, enhancing the peaceful atmosphere of the cabin.

Cabin in Windham

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

Escape to this newly renovated mountain cabin just 5 minutes from Windham Mountain ski resort! With a private fishing pond and a deck offering panoramic resort views, it's a perfect outdoor retreat. Inside, enjoy a pool table, Pac-Man arcade, and shuffleboard for endless fun. A 2-minute drive to town makes dining and shopping convenient. The cabin's modern amenities, cozy fireplace, outdoor firepit, and hot tub guarantee a comfortable and relaxing stay.

4.93 out of 5 average rating, 115 reviews

The exterior of a chalet features a wooden façade with green trim and shutters. A welcoming front door is framed by a small porch, with stacked firewood beside it. Snow blankets the ground, complementing the mountain-style architecture.

Guest suite in Windham

Cozy Cabin Condo by the Mountain, 5mins to skiing!

Steps from the Mountain! Just 1 mile away with a crisp mountain view, our beautiful chalet is a mere 5 minute drive from the slopes of Windham and just 15 minutes from Hunter! A short walk or drive from the charming town of Windham, you're perfectly located for a country getaway. The town itself is a wonderful mountain community with many great shops, restaurants and activities all within a short drive.

4.99 out of 5 average rating, 127 reviews

A grassy field is populated by grazing sheep, with a child seen tending to them. In the background, a rustic cabin with a red roof is set against the backdrop of rolling mountains and overcast skies, surrounded by lush greenery.

Cabin in Gilboa

Panoramic Mountain View Agri-Cabin

Nestled in the serene foothills of the Catskill Mountains, a hidden gem awaits in Gilboa - a charming cabin that embodies the perfect blend of comfort and rustic charm. Clad in warm knotty pine and enriched with hardwood floors, granite countertops, and unique touches like taxidermy and handcrafted stained glass, this cozy retreat beckons you to escape the hustle and bustle of your day to day life.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Windham vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Windham

5 out of 5 average rating, 38 reviews

A cozy living area features a sectional couch set against a wooden wall with a decorative hanging. A warm electric fireplace creates a focal point, while a soft dog bed is positioned nearby. A patterned area rug complements the wooden flooring beneath.

Home in East Durham

Pawfect Family Retreat w/fenced-in yard & Dog Park

5 out of 5 average rating, 68 reviews

A spacious living area features a large green sectional sofa, complemented by decorative cushions. A flat-screen TV is mounted above a stone fireplace. Large windows provide natural light and views of the surrounding forest, while a coffee table is positioned in front of the seating arrangement.

Cabin in Cairo

The Catskill Equestrian Cabin

Superhost

The circular exterior of the home is showcased, featuring large windows that provide abundant natural light. Surrounding greenery and landscaped gardens enhance the inviting atmosphere, while a wraparound deck can be seen above. A well-maintained lawn borders the residence, creating a serene outdoor setting.

4.79 out of 5 average rating, 63 reviews

Designer upstate home perfect for family holidays!

A spacious kitchen features modern blue cabinetry and light countertops, complemented by natural light from large windows. An island with seating offers additional workspace, and hanging cookware is neatly arranged above, providing a practical yet stylish cooking environment.

5 out of 5 average rating, 28 reviews

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

5 out of 5 average rating, 16 reviews

An inviting open-concept living area features two leather sofas and a round accent chair, arranged around a central coffee table. Large windows allow ample natural light to fill the space, revealing views of the surrounding trees. A wood stove is positioned in the center.

Cabin in Hunter

Architect-Designed Cabin Retreat + Grill, Firepit

4.98 out of 5 average rating, 56 reviews

A spacious outdoor deck features comfortable seating with soft cushions and a decorative covered fire pit. A rustic-style birdhouse hangs from the eave, while a pizza oven is placed beside the seating area. Surrounding trees provide a serene backdrop.

Home in East Jewett

Creekside Couple's Retreat w/Hot tub, Sauna & More

A spacious deck rests above a stone patio, bordered by natural stone pillars. The deck features wooden railings and overlooks the outdoor area. Several patio chairs are arranged on the flagstone surface, surrounded by greenery. Windows reflect the sunlight, inviting the outdoors in.

4.78 out of 5 average rating, 83 reviews

Cozy and Charming European Chalet