Vacation rentals in Windham

5 out of 5 average rating, 137 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 Mt Artist Cabin Hiking Kayaking Dining

A storybook cabin, privately nestled in the heart of our beautiful Catskill Mtns, near a babbling stream and lake, under an open sky, surrounded by tall pines was designed me, by a lifelong artist inspired by nature Enjoy endless stars, fires, nearby skiing (Windham Mt Club, Hunter Mt Ski Bowl) swimming, kayaking (CD Lane Park) hiking, dining… OR just relaxing at the cabin...w/high speed wi-fi, indoor+outdoor wood stoves, natural fabrics, antiques, art, full kitch, stone patio, grill, firewood…

4.98 out of 5 average rating, 169 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.

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.

4.89 out of 5 average rating, 154 reviews

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, 211 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.

4.67 out of 5 average rating, 120 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, 173 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.

4.88 out of 5 average rating, 265 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

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.

4.84 out of 5 average rating, 203 reviews

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, 118 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, 342 reviews

Cabin in Lanesville

Only Ski In Out on Mtn | Hike, Golf, Fish, Relax

Mountainside 1 bedroom cabin that fits 4! Ski on/off Hunter Mountain right from your doorstep. Enjoy hiking within a 5-minute drive or walk right onto the mountain from your porch. Unbeatable location on Hunter Mountain, short drive to the picturesque, colorful village of Tannersville, majestic Kaaterskill Falls, and renowned fishing! Fully stocked kitchen/bathroom, full entertainment system with streaming, high-speed WiFi, and dedicated work space.

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.

4.9 out of 5 average rating, 164 reviews

The exterior of a spacious two-story house features a combination of green siding and stone accents. A large deck with seating is visible, surrounded by a landscaped yard with trees and plants. A stone patio area with a fire pit is situated at ground level.

Home in Windham

Original Windham Farmhouse

Direct mountain views and 1 mile to mountain or downtown. Set high-up for privacy, the house has an open concept kitchen/dining and living room. Original timber beams are cozy next to the large gas fireplace. Huge basement recreation room with adjoining bunk room and bath for the kids. SmartTVs, perfect for multiple families, couples or friends. Wander the 10 acre backyard.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

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, 8 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

4.94 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

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, 89 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, 34 reviews

A spacious room features a king-sized bed adorned with simple linens, flanked by two windows with light drapes. A cozy seating area with a lamp and decorative elements is visible. A jacuzzi tub is situated nearby, framed by stone accents and subtle lighting.

Hotel room in Catskill

Giraffe Room - The Old Catskill Game Farm Inn

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

4.96 out of 5 average rating, 28 reviews

A modern living space is highlighted by large windows allowing ample natural light. A cozy sofa is positioned next to a round dining table, with colorful accents and greenery present. Exposed wooden beams add warmth to the open layout, creating a welcoming atmosphere.

Cabin in Hunter

Moritz - Cozy Modern with a Nice View

4.89 out of 5 average rating, 44 reviews

A serene lake reflects the clear blue sky and surrounding green hills. Lush ferns frame the foreground, while a tree stump adds a natural element to the scene. The tranquil water enhances the peaceful ambiance, inviting outdoor activities like swimming and fishing.

Cabin in Windham

Woodside Cabin #2 on Lake Heloise

4.72 out of 5 average rating, 288 reviews

A winding gravel path meanders through a landscape filled with autumn foliage. Tall trees display vibrant orange and yellow leaves, while golden grasses border the trail, creating a serene natural setting. The scene suggests a peaceful retreat into nature.

Condo in Windham

Autumn Retreat w/wood burning fireplace

5 out of 5 average rating, 49 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

4.78 out of 5 average rating, 83 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, 29 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

A modern kitchen features dark wooden cabinetry and stainless steel appliances, including a microwave and oven. A decorative tile backsplash reflects light, while the countertop offers ample workspace. Soft rugs add a warm touch to the wood grain floor, enhancing the functional layout.

4.98 out of 5 average rating, 55 reviews

First Floor Condo with full kitchen.

The open-concept living area features a comfortable sofa, a foosball table, and a dining table made of wood. A modern kitchen with granite countertops and bar seating is visible in the background, illuminated by natural light. Artwork decorates the walls, adding character to the space.