Vacation rentals in Windham

4.98 out of 5 average rating, 156 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, 168 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, 153 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, 376 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 :)

4.92 out of 5 average rating, 100 reviews

A modern kitchen is highlighted by a large island with a quartz countertop and seating. Natural light fills the space through broad windows, offering views of the surrounding greenery. Professional-grade appliances are provided, creating an inviting area for culinary activities.

Vacation home in Windham

*Farmhouse Chic with Mountain and Lake Views*

Welcome to Bright Sparrow Farmhouse! Located on 8 acres of private land with greenery and a wetland lake, this home is the perfect spot to reconnect with nature and enjoy quality time with loved ones. Just mins from Windham and Hunter mountains, you'll be in proximity to the best of the Catskills: skiing, hiking, biking, zip lining, water park, lakes, dining, and winery. Amenities includes business Wifi, gourmet kitchen, washer/dryer, deck w/ bbq grill, outdoor fire pit, badminton, and more.

4.89 out of 5 average rating, 209 reviews

Condo in Windham

Hideaway Windham/Hunter Fireplace Autumn & Foliage

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, 172 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.

5 out of 5 average rating, 317 reviews

A cozy seating area features a large, woven hanging chair with a white cushion and a bright green accent pillow. A textured pouf and a small side table complement the space, which is surrounded by large windows offering views of the mountains and natural light.

Apartment in Freehold

Mountain View Retreat~Sunny Hill Golf / Skiing

Welcome to Sunny Hill Road ! We are located in a small community of private homes in an open space overlooking the mountains. This one bedroom unit has everything you need to enjoy your stay in the Catskills. Relax on the private deck or inside with amazing views from every window. The kitchen is fully equipped and ready to cook a full meal and then enjoy it in the dining room overlooking the mountains. It is quiet and restful here, amazingly beautiful in all four seasons!

4.88 out of 5 average rating, 263 reviews

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

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, 147 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.

4.84 out of 5 average rating, 203 reviews

A living room features a stone fireplace with a wood-burning fire, complemented by a mounted flat-screen TV above. The hardwood floor adds warmth, while artwork of trees decorates the wall. A comfortable couch invites relaxation next to a stack of firewood.

Townhouse in Windham

Redwood Retreat in Windham - minutes to Mtn!

True mountain getaway, just 2.5 hours from NYC!! Spacious 2 bedroom 2 bathroom townhouse minutes to Windham Mountain. Enjoy beautiful wood-burning fireplace, Roku TV and high speed Wi-Fi perfect for remote work. Amenities include outdoor pool (open from Memorial through Labor Day), pickleball, basketball and tennis courts, as well as a fire pit with Adirondack chairs. Very close to town and the amazing escarpment hiking and Elm Ridge mountain bike trails.

4.97 out of 5 average rating, 116 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.

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

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Windham vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Boutique hotels in Windham

Hotel room in East Durham

An elegantly styled entryway features a vintage bench with a cushion, set against a deep blue wall adorned with an ornate mirror. The floor showcases a patterned tile design complemented by a rich red area rug, while a staircase leads to the upper level.

5 out of 5 average rating, 7 reviews

The Onyx Room Luxury in the Catskills

4.91 out of 5 average rating, 57 reviews

A spacious queen room is furnished with a comfortable bed, accented by a colorful area rug. A window offers natural light, and a sitting area features a modern chair and side table. A small desk is positioned near the room's entrance.

Hotel room in Hudson

The Howard Hotel Hudson - Room 301

A cozy sleeping area is furnished with a spacious bed adorned with white linens and a decorative yellow pillow. A wooden desk with a green chair is positioned against a wall, complementing the light-colored shiplap and soft green paint. A few framed artworks are displayed.

Hotel room in Mount Tremper

4.8 out of 5 average rating, 5 reviews

Farmhouse Inn in the Heart of the Catskills (Rm 8)

5 out of 5 average rating, 4 reviews

The guest room features an elegant antique French four-poster bed with a delicate quilt. A vintage tapestry couch and matching armchair provide additional seating. Decorative elements include soft lighting and floral wallpaper, enhancing the room's stylish character. Large windows allow natural light to filter in.

Hotel room in Saugerties

Regal Romantic Luxury Victorian Getaway Catskills

4.98 out of 5 average rating, 88 reviews

A cozy suite is showcased with a spacious bed featuring decorative pillows and a textured blanket. A comfortable seating area is provided with a sofa and chairs. Natural light filters through large windows, and decorative plates adorn the wall above the bed.

Hotel room in Kingston

Grace and Favor - welcoming one bedroom suite

4.92 out of 5 average rating, 65 reviews

An outdoor patio area is covered with a wooden pergola, featuring seating arrangements with comfortable chairs and small tables. Potted plants add greenery, while a staircase leads to additional accommodations. Umbrellas provide shade, enhancing the inviting atmosphere for guests.

Hotel room in Saugerties

Village Inn - Tribeca suite - Saugerties NY

A modern sleeping area features a double bed with a tufted headboard and light bedding. A sliding barn door is positioned nearby, with a clock mounted on the wooden wall. Soft lighting from wall sconces enhances the warm tones of the wooden beams above.

Hotel room in Stamford

4.76 out of 5 average rating, 93 reviews

The Vine on Main, The Planker room.

Hotel room in Mount Tremper

An outdoor seating area is surrounded by vibrant gardens, featuring bright pink lounge chairs and tables arranged on a brick patio. A fenced saltwater pool is visible in the background, framed by greenery and situated near decorative lighting.

4.81 out of 5 average rating, 59 reviews

Catskill Rose Lodging & Dining

Other great vacation rentals in Windham

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.

4.95 out of 5 average rating, 56 reviews

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

5 out of 5 average rating, 36 reviews

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

Mountainside Farmhouse: 2 BR w/ Loft on 4.3 Acres

4.9 out of 5 average rating, 61 reviews

An aerial view showcases the chalet's exterior surrounded by lush greenery. The large garden is visible with a gravel driveway leading to the entrance. Outdoor seating areas are arranged on the patio, complemented by a stylish deck overlooking the expansive lawn.

Chalet in Windham

Rustic Mountain view Cabin 5 mins to Ski Area!

5 out of 5 average rating, 11 reviews

The living area features a cozy arrangement with a gray sectional sofa and an orange armchair, inviting relaxation. A modern television is mounted above a black fireplace, which is framed by natural wood accents. Large windows allow natural light to fill the space, showcasing rustic wall textures.

Cabin in Ashland

Luxury Cabin Retreat - 7 Mins to Windham

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.

4.8 out of 5 average rating, 64 reviews

Designer upstate home perfect for family holidays!

5 out of 5 average rating, 19 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

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