Vacation rentals in Windham

4.95 out of 5 average rating, 104 reviews

The open living area features elevated ceilings with wooden beams and large windows flooding the space with natural light. A wood-burning fireplace is positioned beneath a wall-mounted TV, flanked by two rocking chairs and a circular coffee table set on a textured area rug.

Townhouse in Windham

Lothbrok - the "B" side - 2 mile slopes & town

5 min to Windham Mountain / easy 15-19 min to Hunter! 1 mile to Windham's Main Street - restaurants, pubs, movie theatre & shopping. Remodeled with luxury vinyl flooring, low VOC paint, LED lighting, Culligan water treatment, excellent cell phone service & FREE WiFi means no issues making calls/texts/internet. We kept some of the groovy charm of the 1970's (spiral stairs) and brought the house into this century looking brand new again. NOT SAFE for babies, children under 12 or pets. No smoking.

5 out of 5 average rating, 139 reviews

An inviting living area features wooden beams and warm tones. A comfortable sofa with decorative pillows faces a wood stove, while a well-equipped kitchen is visible in the background. Light filters through multiple windows, highlighting the natural wood cabinetry and charming kitchen appliances.

Guesthouse in Windham

Catskill Mts Artist Cabin: Fall Hiking, Dining…

Here now Beautiful Fall exploring, hiking, outdoor dining and farm mkts. Our storybook cabin is privately nestled in the heart of the Catskill Mtns, near a seasonal stream and lake, under open sky, surrounded by forest, Enjoy very nearby skiing (Windham Mt, Hunter Mt.) swimming, kayaking, hiking, dining, mkts. Experience true quiet, endless stars, indoor and outdoor wood fires, complimentary firewood, natural fabrics, authentic art/vintage design, full kitchen, rain shower, stone patio, grill…

4.88 out of 5 average rating, 158 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.

4.9 out of 5 average rating, 217 reviews

Condo in Windham

Hideaway Windham/Hunter Fireplace, Snow & Skiing

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.

4.67 out of 5 average rating, 121 reviews

A spacious outdoor deck is visible, furnished with a round table surrounded by several chairs and a lantern on top. A comfortable seating area with a couch is positioned nearby, set against a backdrop of lush greenery.

Condo in Windham

Windham Condo

This condo is right off Route 23, minutes from Windham Mountain. Head to the Catskills to enjoy the great outdoors. The complex has a pool, 2 tennis courts and a fire pit. Enjoy the mountain air while working from home with dedicated Wifi. We have a well-stocked kitchen, wood-burning fireplace, and comfy deck. You are in place to enjoy all the skiing, hiking, mountain biking, and golf Windham has to offer. Only 2.7 miles from Windham Mountain Resort. Guest ID may be required on arrival.

4.99 out of 5 average rating, 179 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, 323 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, 271 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

4.98 out of 5 average rating, 132 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, 116 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.

4.98 out of 5 average rating, 607 reviews

A restful bedroom is presented with a wooden bed featuring a quilted navy coverlet. Two bedside sconces provide soft lighting. Windows allow natural light to enter, complemented by neutral walls and dark curtains. A small shelf is mounted beside the bed for convenience.

Condo in Lanesville

Trendy Condo Hunter Mountain

Newly renovated modern condo slope-side at Hunter mountain. Come enjoy the beauty of the Catskills & winter events while staying at our cozy and stylish condo. Warm up by the electric fireplace, fix a meal and have a drink in our brand new kitchen, watch a movie, and enjoy a restful sleep in a relaxing bedroom.

4.96 out of 5 average rating, 383 reviews

A living room features a comfortable brown sofa and a patterned area rug. A large flat-screen TV is mounted on the wall, while a stone fireplace serves as a focal point. Windows with light curtains allow natural light to fill the space.

Chalet in Hensonville

2BDR- Cozy Windham/Hunter Escape

The Windham Escape is a cozy 2 bedroom apartment nestled in the northern Catskill Mountains. It is close to restaurants and dining, great views, family-friendly activities, Hiking, Skiing, Golf and other outdoor activities. Our place is great for friends traveling together, couples, and families (with kids).

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, 9 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

4.78 out of 5 average rating, 45 reviews

A spacious bedroom features a king bed with light bedding and a wooden frame. Large windows allow natural light, illuminating the warm wooden floor. A separate living area is visible through the open doors, showcasing a cozy seating arrangement and a desk.

Hotel room in Hudson

Hudson Mariner Suite 1

4.94 out of 5 average rating, 49 reviews

An outdoor patio area is enclosed by a wooden pergola, providing shade. Below, outdoor furniture, including lounge chairs and a table, is arranged for relaxation. Potted plants add greenery, and a staircase leads to the second floor, blending the outdoor space with the building.

Hotel room in Saugerties

Village Inn - Chelsea suite - Saugerties NY

4.98 out of 5 average rating, 94 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

5 out of 5 average rating, 5 reviews

A cozy sleeping area features a queen brass bed adorned with a floral patterned quilt. Antique furniture, including a side table and a trunk, complements the oak paneling. Plush seating is arranged around a small antique table, all illuminated by warm lighting from vintage lamps.

Hotel room in Saugerties

Catskills Getaway - Spacious Comfortable Room

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

4.77 out of 5 average rating, 95 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.

4.82 out of 5 average rating, 60 reviews

Catskill Rose Lodging & Dining

Other great vacation rentals in Windham

5 out of 5 average rating, 3 reviews

Home in Windham

Scenic Home 2 mins from Wdm Mtn

5 out of 5 average rating, 26 reviews

Cabin in Hunter

Architect-Design Cabin in the Woods + Fireplace

5 out of 5 average rating, 53 reviews

A spacious living area contains a light grey sofa with decorative pillows and a wooden coffee table on a patterned rug. Large windows allow natural light to filter in, highlighting a green potted plant. A red wood stove is visible on the side.

Cottage in Windham

Cozy Cottage Retreat Close to Main St/Windham Mtn

4.92 out of 5 average rating, 72 reviews

A historic building with a light exterior features multiple large windows and patios for outdoor seating. The ground level displays inviting storefronts and flag decorations, while trees frame the structure, enhancing its charming presence along Main Street.

Apartment in Windham

Right on Main Street! 2mins to MTN

4.97 out of 5 average rating, 70 reviews

A bright living space features a cozy alcove with built-in benches, adorned with plush cushions. A smooth, rounded fireplace stands prominently, its flames flickering warmly. Natural light pours in through the two windows, illuminating wooden accents and rustic chests positioned around the room.

Home in East Jewett

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

4.78 out of 5 average rating, 87 reviews

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.

Home in Windham

Cozy and Charming European Chalet

4.97 out of 5 average rating, 35 reviews

A cozy retreat is set against a backdrop of lush greenery. The red exterior of the house is complemented by large windows and a deck featuring outdoor seating under umbrella shades. A hammock is suspended among the trees, offering a serene resting spot.

Cabin in Cornwallville

Cozy 2-Bedroom Mountain Escape