Holiday rentals with outdoor seating in Kingston

5 out of 5 average rating, 102 reviews

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

A cozy bedroom features a spacious bed with layered bedding. A gallery wall of framed art pieces adds visual interest. Natural light filters through a window with shutters, illuminating the warm wood floors. An electric fireplace and a potted plant provide a touch of comfort.

4.97 out of 5 average rating, 342 reviews

The Ivy on the Stone

The oldest house you can stay at in the historic heart of Kingston! Walkable! This landmark 1680 stone house has been featured in Upstate Diary and Houzz. Enter this 350 sq ft luxe apartment through a secret garden and a shared porch. The private spa-like bathroom features a clawfoot tub, and rain shower. Featuring an organic queen bed, an electric fireplace, workspace, William Morris wallpaper, and a Nespresso maker. If you want to stay in the larger house visit: https://abnb.me/EexspArCAIb

A spacious living room features large windows allowing natural light to fill the area. A grand piano is positioned near a comfortable seating arrangement, which includes a sofa and chairs. A decorative area rug adds warmth, while framed artworks adorn the walls.

4.97 out of 5 average rating, 114 reviews

Large 2-BR apartment in historic waterfront home

This sophisticated, cozy, pet-friendly historic home in Kingston's beautiful, walkable downtown waterfront (Rondout National historic district) is close to restaurants, sidewalk cafes, boutiques, parks, a beach, museums, galleries, and more. It features a beautiful front porch and back deck, fenced-in yard, living room, master bedroom (queen bed), 2nd bedroom with (full-sized bed), and den/study adjacent to the second bedroom. It is the perfect retreat for a couple, friends, or a small family.

4.91 out of 5 average rating, 570 reviews

A living area features a comfortable sectional sofa adorned with cushions and a low wooden coffee table. Natural light fills the space through two windows, while a floor lamp provides additional illumination. The interior is accented by warm, earthy tones and wooden flooring.

Flat in Stone Ridge

Romantic Apartment in Historic Stone Ridge

Relax in this cozy apartment in our beautiful colonial house in the middle of historical Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original art. Full kitchen is equipped with everything you need to prepare a great meal. It is perfect for all seasons and located within walking distance to restaurants, coffee shops, yoga studios, groceries. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

A serene living space features wooden walls and ceiling, creating a warm ambiance. A low circular table is centered on a light area rug. Two large windows allow natural light to illuminate potted plants, enhancing the peaceful environment.

4.97 out of 5 average rating, 144 reviews

The Zen Den in Historic Rondout District

Escape to charming Kingston, NY and stay in the garden apartment of our historic brick home built in 1880. The womb like studio has heated clay floors and a floating cabin bedroom that will envelop and soothe. The private backyard with stonescaping and fire pit is yours alone to enjoy. Walk down the waterfront promenade to the Strand district with shops, restaurants, and museums, or drive to the surrounding swimming holes and nature trails of Woodstock, Rosendale, High Falls, and Saugerties.

5 out of 5 average rating, 244 reviews

A spacious master bedroom is shown, featuring a large white bed with crisp bedding positioned against a light gray wall. Warm lighting is provided by bedside lamps. A decorative mirror reflects the room, and hardwood flooring is complemented by a soft area rug.

Guest suite in Kingston

Calm Oasis, walk to Historic Stockade

Relax, rejuvenate and refresh in your own private, spacious master suite and living area. This beautiful, welcoming space has been 100% renovated with guests in mind. Serene natural color scheme, warm lighting, and ample natural light. Decorated with tasteful furnishings. 15 min. walk to the center of the historical Stockade District. Additional rules No pets, we have two cats, they will be very stressed to hear or smell another animal in the house. City of Kingston STR Licence #008390

4.99 out of 5 average rating, 160 reviews

A private cabin is nestled among lush greenery, showcasing a large deck with two Adirondack chairs positioned for relaxation. The cabin features large glass doors that open to the natural surroundings, enhancing the peaceful atmosphere.

Guest house in Kingston

Chic, Private Cabin with Stunning River Views

Private, fully renovated cabin with high-end finishes and stunning views of the Hudson River. All creature comforts including full kitchen, expansive living room, stylish bathroom and cozy bedroom, along with firepit and large deck to watch the eagles from. Nestled on a wooded corner of the owner's property but completely independent with separate driveway, parking and fenced yard for privacy. Just minutes from shopping/dining in Kingston, as well as world world class hiking and nature.

The historical frame house showcases a charming exterior with a blue wooden facade, surrounded by snow-covered trees. A winding road leads to the entrance, while decorative lampposts and a nearby yellow house frame the scene, creating a peaceful winter atmosphere.

4.98 out of 5 average rating, 174 reviews

Historical Walkable Stockade Retreat • c.1811

Capture a slice of Kingston's heritage in this historical frame home, built in 1811 by the sheriff for his daughter. Thoughtfully updated, the house retains beautiful period details like double-hung windows, Federal-style staircase, and decorative fireplaces—all paired with comfortable, contemporary furnishings. Family-friendly amenities make it a great spot for travelers of all ages. A charming house filled with character and history for you to enjoy—just be patient with her quirks!

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.

4.97 out of 5 average rating, 146 reviews

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

A welcoming entrance to the home is framed by a red door and a decorative lantern. Lush greenery and vibrant red flowers are visible in planters, contributing to the serene outdoor setting. The backdrop features a brick building with large windows and climbing plants.

4.97 out of 5 average rating, 357 reviews

DeMew House in Historic Kingston

PRIVATE, ELEGANT ONE KING BEDROOM HOME! DeMew House is an exclusive renovated 1850s brick home, a block from the historic Kingston waterfront. Enjoy total privacy in an elegant, transitional two-story home with an open floor plan that is inviting, warm and intimate. The home, across from a marina, has a king bedroom, a pull-out sofa bed, an en suite bathroom with two-person shower and double vanity. A full kitchen, ac, private driveway and gazebo frame this discerning getaway...

A spacious bedroom features a queen bed adorned with simple linens. A large wooden barn door provides entry to the adjoining room. Two comfortable chairs sit beside a sleek television stand, with natural light filtering through large windows framed by greenery.

4.96 out of 5 average rating, 409 reviews

Dog Friendly Uptown Apt Near Stockade + Backyard

2 hours from NYC, escape to this pet-friendly outdoor oasis in Uptown Kingston only a short walk from the Historic Stockade District. Renovated in 2020, this 1-bedroom apartment is accented with vintage decor, indoor plants and has a huge backyard for your pup. Use the full kitchen or walk to the many restaurants in the Stockade. The expansive backyard includes a stone patio, outdoor table for dining, Adirondack chairs & hammock. Free driveway parking, WIFI, and Netflix!

A well-lit bedroom features a spacious bed covered with a soft white comforter. A large mirror leans against the wall, reflecting natural light. In the foreground, a vibrant green plant adds a touch of nature. The doorway leads to an inviting living area with warm lighting.

4.79 out of 5 average rating, 164 reviews

Comfy 2-BR Apt. Cozy & Convenient

Indulge in the charm of our delightful Kingston, NY apartment! Relax in two luxurious full beds amidst stunning trails, exquisite dining, and charming boutiques. Immerse yourself in vibrant Midtown, steps from the historic Stockade District. Rejuvenate, cook in our well-equipped kitchen, or dine on the private patio. Book now for an unforgettable stay! FUN FACT: Discover the fascinating historical gem of America's oldest corner, just a leisurely 10-15 minute stroll away.

Popular amenities for outdoor seating rentals in Kingston

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.97 out of 5 average rating, 259 reviews

Retro-Chic Cabin in Woodstock - Sauna

A bright dining area features a long white table surrounded by wooden chairs. Large glass doors open to a deck with river views. Sunlight fills the space, highlighting the clean lines of the cabinetry and décor in soft, neutral tones.

4.93 out of 5 average rating, 180 reviews

Upstate Waterfront Saugerties Retreat-Near HITS

The living area showcases large windows with original trim, allowing ample natural light. A cozy orange couch is paired with a small black coffee table, complemented by two blue armchairs. Natural wood flooring and a geometric rug add warmth and texture to the space.

4.92 out of 5 average rating, 107 reviews

Peaceful Retreat in the Heart of Kingston

A wooden dock extends into the calm waters of the Esopus Creek, surrounded by lush greenery. The tranquil surface of the water reflects the surrounding trees, creating a serene atmosphere. Smooth stone steps lead down to the water's edge, enhancing accessibility.

4.97 out of 5 average rating, 317 reviews

Creekside Cottage

The farmhouse exterior features a spacious porch with steps leading down to a grassy area. The surrounding landscape includes trees, providing a natural setting. Large windows allow for plenty of natural light, enhancing the home's open feel.

4.92 out of 5 average rating, 287 reviews

Beautiful farmhouse with Mountain View- HITS- AC

An inviting living area features a light gray sofa accented with blue pillows, positioned on hardwood flooring. Visible to the left, a wooden dining table and chairs complement the modern kitchen with dark cabinetry. The loft above includes a workspace with a view of the lower level.

4.96 out of 5 average rating, 165 reviews

BRAND NEW! This New House Three

4.91 out of 5 average rating, 748 reviews

The exterior of the cottage is shown, featuring rich wood paneling and large glass doors. A stone pathway leads to a charming seating area, which includes a decorative bench. Lush greenery surrounds the property, enhancing the natural environment.

Home in Woodstock

Dutch Touch Woodstock Cottage

4.98 out of 5 average rating, 103 reviews

A warm and inviting living space is seen, featuring a round wooden dining table surrounded by four rustic chairs. An adobe wood-burning fireplace is visible in the background, with seating arranged nearby for relaxation. Natural light flows in through a window, enhancing the cozy atmosphere.

Home in East Jewett

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

Apartment rentals with outdoor seating

A spacious living area features a futon decorated with patterned cushions and a striking red pool table. A light fixture with multiple bulbs hangs overhead, while a wall-mounted TV is visible in the background. Large pocket doors separate the living space from the bedroom.

4.98 out of 5 average rating, 201 reviews

Lovely 1 bedroom apt. with free parking in Rondout

A comfortable living room features a cozy couch, armchair, and a coffee table set on a patterned rug. A wall-mounted 50-inch smart TV is visible, along with two windows allowing natural light to brighten the space. Decorative lamps add to the ambiance.

4.98 out of 5 average rating, 125 reviews

Kingston Aerie: 2BR charmer, quiet and lovely

4.92 out of 5 average rating, 378 reviews

A well-lit patio space features a wooden table with a gas fire pit at its center, surrounded by four wicker chairs. Natural stone walls and a flower-adorned fence provide a backdrop, while soft lighting enhances the cozy atmosphere.

Flat in Saugerties

Saugerties Village home with great backyard!

4.88 out of 5 average rating, 336 reviews

A cozy eat-in kitchen features a round table set for two, with a bouquet of flowers at the center. Light filters through a nearby window, illuminating the space. A refrigerator and kitchen cabinets are visible in the background, creating a functional atmosphere.

Flat in New Paltz

Homey Haven:Inviting Airbnb Suite with kitchen

4.78 out of 5 average rating, 662 reviews

The exterior of a historic stone farmhouse is shown, featuring a vine-covered wall and landscaped garden. Steps lead to the entrance, surrounded by greenery and floral elements, with large windows allowing natural light. The serene outdoor setting reflects the charm of the surrounding countryside.

Flat in High Falls

Art Room at Old Stone Farmhouse

An outdoor space features a hot tub surrounded by a gravel area. Two lounge chairs and a glass table are placed near a striped rug. Potted plants are hung along the wooden fence, enhancing the cozy atmosphere.

4.88 out of 5 average rating, 216 reviews

Charming Pet Friendly Getaway w Hot Tub & Fire Pit

4.96 out of 5 average rating, 411 reviews

The living area features a welcoming sofa set with soft, rounded chairs and a wooden coffee table. A rustic accent wall made of horizontal wooden planks adds character. Natural light fills the space, highlighting the art pieces and decor. A workspace is visible in the background.

Flat in New Paltz

Modena Mad House

4.89 out of 5 average rating, 239 reviews

Flat in Newburgh

Special Nest w Private Entrance River View Porches

Apartment rentals with outdoor seating

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.

5 out of 5 average rating, 29 reviews

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

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.

4.67 out of 5 average rating, 123 reviews

Windham Condo

5 out of 5 average rating, 60 reviews

A spacious living area includes a large green sofa, a wooden coffee table, and a soft rug underfoot. Natural light enters through two windows, illuminating the space. A dog lounges comfortably on the rug, while stylish seating options are arranged around the table.

Apartment in Kerhonkson

Hike Minnewaska + Walk to Rail Trail, Food, Drink

A modern kitchen is featured, showcasing wooden cabinetry and stainless steel appliances. A countertop with a coffee maker and a wooden table is visible. Light streams through the window, illuminating the space that is designed for convenience and efficiency.

5 out of 5 average rating, 62 reviews

Lothbrok - 2nd floor on Main Street

4.83 out of 5 average rating, 80 reviews

A view from the private sundeck overlooks a serene lake with reflections of surrounding trees. The warm glow of the setting sun casts long shadows on the wooden deck, enhancing the natural beauty of the landscape.

Apartment in Hunter

Perfect Catskills hiking getaway with fireplace

4.86 out of 5 average rating, 65 reviews

The living area features a gray couch adorned with colorful cushions, a wooden coffee table, and a black chair. A world map hangs on the wall above the cozy wood-burning fireplace, and natural light enters through the nearby window, partially covered by sheer curtains.

Apartment in Lanesville

Slopeside Condo with wood fireplace

4.98 out of 5 average rating, 58 reviews

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.

Apartment in Hunter

Walk to Hunter Mtn Slopes (5 Min) + Fireplace

An inviting outdoor hot tub is positioned on a wooden deck, overlooking expansive views of the lush Catskills. The serene water bubbles gently, with the surrounding trees and distant mountains creating a tranquil backdrop.