Holiday rentals with outdoor seating in Windham

4.97 out of 5 average rating, 178 reviews

An open floor plan living area features vaulted wooden ceilings and large windows offering views of the outdoors. Comfortable seating areas include a tan couch, black chairs, and a decorative coffee table. A dining space with a large table and an island kitchen is also visible.

Chalet in Windham

Gorgeous Lodge | Mt View, HotTub, Firepit, Game Rm

Plan your all-seasons escape to this gorgeous new mid-century modern chalet with can't-beat direct views of Windham Mtn, less than a 5 minute drive away. Situated between state land and an active creek, enjoy this mountain getaway's hot tub, firepit, game room, open floor plan and other luxury amenities. Just 2.5 hours from NYC, and minutes away to skiing (<5 min to Windham Mtn, 15 min to Hunter Mtn, 40 min to Belleayre Mtn), hiking, biking, swimming, golfing, fishing, vineyards and restaurants!

ValueLocationBarbecue

5 out of 5 average rating, 234 reviews

Home in Hunter

Embrace nature in style @ #killercatmountainhouse

Natural splendor meets seductive style at #killercatmountainhouse, a design-focused retreat 5 minutes from Hunter Mountain—and 13 minutes to Windham Mountain—that delivers a fresh & unexpected Catskills experience. Embrace summer from our expansive deck, hot-barrel sauna, fire pit & roomy hot tub, or unwind by the fireplace w/records & games. Our Parisian-chic décor provides Insta-worthy moments inside & out, while our epic views & amenities allow outdoor enthusiasts to indulge all season long.

LocationOutdoor spacesQuiet

5 out of 5 average rating, 152 reviews

A warm bedroom is framed by sloped wooden ceilings and contains a spacious bed adorned with plush bedding. Two bedside lamps provide soft light, accentuating the wooden decor. A round window offers a view of the trees outside, enhancing the natural ambiance.

Guesthouse in Windham

Catskill Mts Artist Cabin Hike Dine Star Firegaze

June ! Hiking, Kayaking Outdoor Dining In Town Or Patio under Starry sky w/Woodfire …Our storybook cabin is privately nestled in heart of the Catskill Mts, near seasonal stream and lake, under open sky surrounded by forest. Enjoy very nearby skiing; Windham and Hunter Mts, hiking, dining, antique, farm mkts. Experience true quiet, endless stars, staring into a wood fire, w/complimentary firewood, natural fabrics, authentic art/vintage design, full kitchen, rain shower, stone patio, grill.

Outdoor spacesValueCheckout

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.

5 out of 5 average rating, 406 reviews

Private cabin in the Catskills

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 :)

Outdoor spacesLocationDecor

4.99 out of 5 average rating, 129 reviews

A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.

Home in Staatsburg

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Outdoor spacesLocationGetting around

4.95 out of 5 average rating, 499 reviews

An aerial view captures the chalet, surrounded by a lush, open green lawn. Trees line the property, providing a natural border. The distant mountains and hills are visible, with a gentle gradient of colors as sunset approaches, suggesting a serene rural setting.

Cabin in Windham

CozyCatskillChalet w/ Hot Tub (Catskill Mountains)

At face value, IG: @cozycatskillchalet appears to be just a humble little getaway tucked in the Catksill Mountains of Windham, NY. But even the most discerning guests will be quickly spirited away by the rustic charm and postcard-eqsue surroundings all around. At night, can't-be-beat stargazing on the back deck (or while soaking in the hot tub) will have you convinced this humble hideaway is a lot more illustrious than it lets on. Disclaimer: The chalet is not a luxury hotel or property.

LocationOutdoor spacesLaundry

4.91 out of 5 average rating, 117 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.

Holiday 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. Enjoy skiing, hiking, biking, zip lining, water park, lakes, dining, and winery. Our home is a sustainable retreat, powered by solar energy and equipped with a backup battery system. This means you'll enjoy a comfortable and uninterrupted stay.

LocationValueAir conditioning

4.96 out of 5 average rating, 214 reviews

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.

Home in Hunter

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!

LocationValueGetting around

4.98 out of 5 average rating, 195 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.

LocationOutdoor spacesTV

4.9 out of 5 average rating, 100 reviews

A single-story home is set amidst lush greenery, featuring a wooden deck with a roof and a ramp leading to its entrance. Well-maintained flower beds surround the entrance, while a spacious lawn extends into the background.

Home in Jewett

Sweet cottage near Hunter Mountain

This is our home away from home where we love to go in our free time. The house is 10 min drive from Hunter mountain or Windham. Great for skiing in winter / hiking in summer. WiFi: YES! High speed internet, Fiber Optic, 200Mbps. Perfect for work from home. Netflix, Disney+ and great selection of movies is available for all guests which you may enjoy on new 75 inch TV. Great for movie nights! Sound system through out the house is also available. Baby equipment upon request.

Outdoor spacesLocationCondition

4.95 out of 5 average rating, 206 reviews

Cabin in Windham

Cozy 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.

LocationOutdoor spacesHospitality

4.99 out of 5 average rating, 134 reviews

Home in East Jewett

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

Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

LocationValueHiking

Popular amenities for Windham outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.98 out of 5 average rating, 179 reviews

A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.

Home in Kingston

Hillside Views in Hudson Valley

LocationOutdoor spacesSolo travel

The image displays a charming red house with two stories, featuring a welcoming front porch with white railings. A snow-covered yard surrounds the home, while a large tree is positioned to the left. The clear blue sky adds to the serene atmosphere.

4.9 out of 5 average rating, 136 reviews

Big Red Retreat 3 min to Windham Mountain & Golf!

LocationValueHiking

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.

4.97 out of 5 average rating, 107 reviews

Windham Farmhouse Escape

Outdoor spacesLocationFamily

An open living area showcases a wooden ceiling with beams and a rustic dining table surrounded by black chairs. A cozy couch faces a brick fireplace, while a modern kitchen with stainless steel appliances is visible in the background. Soft lighting from a chandelier adds warmth to the space.

4.8 out of 5 average rating, 127 reviews

Mountain Chalet Retreat New Hot Tub

ValueLocationHiking

4.94 out of 5 average rating, 388 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

LocationOutdoor spacesView

4.99 out of 5 average rating, 135 reviews

The A-frame chalet is framed by lush greenery, featuring a dark exterior with large windows. A bright blue door welcomes guests, and a private balcony extends from the upper level. Natural light reflects off the exterior, highlighting the home's inviting design.

Home in Prattsville

Scandi A-Frame w/Hot Tub & Sauna

ValueOutdoor spacesAccess

Home in Hunter Mountain, Hunter

A spacious deck features a glass-top dining table surrounded by four chairs, inviting outdoor dining. Lush greenery and rolling hills are visible in the background, complemented by a blue sky adorned with white clouds, creating a serene natural setting.

4.97 out of 5 average rating, 121 reviews

Pet Friendly, Close to Hiking and Mountain Lakes

Outdoor spacesLocationBackyard

4.99 out of 5 average rating, 159 reviews

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

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

ValueOutdoor spacesBarbecue

Apartment rentals with outdoor seating

4.92 out of 5 average rating, 211 reviews

A cozy bedroom features a spacious bed with light grey bedding, accompanied by a side table and a soft glow from a nearby lamp. Sunlight filters through sheer white curtains, illuminating the warm wood floor. A doorway leads to the private bathroom, visible on the right.

Apartment in Catskill

Catskill Village House - Studio w/ Private Terrace

LocationValueAccess

4.99 out of 5 average rating, 177 reviews

Apartment in Acra

Burnt Knob Mountain Escape

LocationOutdoor spacesCheckout

5 out of 5 average rating, 353 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

LocationValueParking

4.99 out of 5 average rating, 155 reviews

A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.

Apartment in Coxsackie

Hudson River Beach House

ValueLocationFamily

4.99 out of 5 average rating, 451 reviews

A modern studio features a spacious bed draped in white bedding with blue accents, alongside a cozy seating area with a dark sofa. Floor-to-ceiling glass windows provide stunning views of the river and open onto a private terrace, enhancing the serene ambiance.

Apartment in Ulster Park

Escape to a Sleek, Serene Studio on the Riverbank

Outdoor spacesLocationRiver

4.76 out of 5 average rating, 155 reviews

A charming house features a front porch with steps leading to the entrance. Lush greenery surrounds the building, while a wooden fence borders the yard. The exterior showcases a mix of dark wood and white trim beneath a blue sky.

Apartment in Windham

Catskill Getaway, Ski Windham & Hunter Mountains

ValueOutdoor spacesFamily

4.91 out of 5 average rating, 149 reviews

Apartment in Hunter

Cozy Clean apt 5 min to Hunter Dog Heaven

Outdoor spacesValuePets

4.97 out of 5 average rating, 178 reviews

A living room is presented with a leather couch and two orange chairs arranged for conversation. A stone fireplace serves as a focal point, complemented by two framed art pieces on the wall. A patterned rug is located beneath a wooden coffee table, enhancing the space's design.

Apartment in Cairo

Foothills of the Catskills

Outdoor spacesValueGetting around

Condo rentals with outdoor seating

5 out of 5 average rating, 30 reviews

A bright living area is featured, showcasing a cozy arrangement of gray sofas around a circular coffee table. A modern ceiling fan circulates air above while large windows reveal stunning valley views, allowing natural light to fill the room. An electric fireplace adds warmth to the space.

Condo in Windham

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub

LocationViewIndoor spaces

A multi-level chalet-style building features a blend of wood and stone exteriors. Large windows enhance natural light, and several balconies overlook a lush green landscape. A wooden bridge leads across a small waterway, connecting seamlessly to the surrounding nature.

4.86 out of 5 average rating, 152 reviews

Trailside At Hunter-Phase II-Hunter NY

LocationValueBathroom

4.67 out of 5 average rating, 123 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

ValueOutdoor spacesQuiet

The studio features a compact kitchen with modern appliances and a dining island with seating for three. A cozy seating area includes a firm couch and a coffee table, while a wall-mounted TV is positioned nearby. Natural light fills the space, enhancing its welcoming ambiance.

5 out of 5 average rating, 23 reviews

Hunter creekside condo with mtn. view

LocationComfortNearby

4.97 out of 5 average rating, 703 reviews

A modern living area features a dark blue sofa and a coffee table with decorative items. The open kitchen showcases stainless steel appliances and a dining area with four bar stools. Warm lighting enhances the inviting space, while wall art adds character.

Condo in Lanesville

Ski on/ Ski off Country Condo Hunter Mountain

Outdoor spacesLocationCleanliness

The exterior of the condo is showcased, featuring a two-story structure with a combination of red siding and stone accents. Balconies with wooden railings extend from the upper levels, and a prominent stone chimney rises against a cloudy sky.

4.96 out of 5 average rating, 74 reviews

Hunter Mountain 2BR Condo - Steps to Ski Slopes!

Outdoor spacesValueCondition

The entrance to the condo is highlighted by a wooden deck with railing, leading to a door framed by a welcoming outdoor area. Nearby, a path is visible, bordered by neatly trimmed grass and bushes, providing easy access to the parking area.

4.98 out of 5 average rating, 61 reviews

Walk to Hunter Mtn Slopes (5 Min) + Fireplace

LocationOutdoor spacesHiking