Holiday rentals with outdoor seating in Highland Falls

4.99 out of 5 average rating, 126 reviews

A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.

Cottage in Warwick

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

4.99 out of 5 average rating, 103 reviews

A contemporary two-story home is presented, featuring a combination of wood and gray siding. Stone steps lead to an inviting entrance, while surrounding greenery provides a natural backdrop. Large windows allow for ample natural light, enhancing the exterior's modern design.

Home in Highland Falls

Modern 3BD West Point USMA House w/ HotTub!

Our beautiful 3 bed, 2 bath contemporary home sits just 0.4 miles from West Point Military Academy. The house is equipped with super fast internet, work stations in each bedroom, cozy nectar mattresses, a 4-person jacuzzi, and of course, an incredible back yard patio with a BBQ, fire pit and outdoor dining area. Our kitchen is stocked for coffee lovers with 3 different types of machines ( Nespresso, Keurig, and Miele). There are also Samsung Smart TV's in each bedroom along with Sonos speakers!

4.97 out of 5 average rating, 108 reviews

The exterior of the house is surrounded by trees, with a welcoming front porch featuring chairs. A circular stone fire pit area is visible in the yard, complemented by a gravel surface and wooden adirondack chairs. The driveway is paved and leads to the garage.

Home in Highland Falls

West Point Mountain House

Welcome to West Point! Enjoy early check-in in and late check out at our beautiful mountainside house overlooking the village on its own private hill. Spacious & cozy, this house is great for large families or groups of friends coming to explore West Point, Bear Mountain, Storm King, or the Hudson Valley at large. Just 1 hour from NYC and minutes away from restaurants and local attractions. This 3500 Sq Foot home features fun for everyone in a private setting, yet still close to all the fun!

Apartment in Highland Falls

A spacious living area is furnished with a dark sofa and decorative pillows, complemented by a light wooden coffee table. A large mirror reflects natural light, while floor lamps provide additional illumination. The room features light-colored walls and sleek wooden flooring, enhancing the open feel.

4.83 out of 5 average rating, 285 reviews

Stylish affordable 2BR Steps from Thayer gate+prkg

Welcome to your stylish retreat in the heart of Highland Falls! This beautiful 2-bedroom apartment boasts a wide-open layout framed with breathtaking Mountain View’s just steps from the entrance to the Military Academy. Whether you're here to visit family, explore the Hudson Valley, or simply relax on your own, this perfect location provides the best blend of comfort, convenience, and style. With fast WIFI, private parking and no cleaning fee, your stay will be both affordable and stress-free!

4.99 out of 5 average rating, 176 reviews

A hammock is suspended between two trees, providing a relaxing spot beside the lake. Vibrant autumn leaves in shades of orange and yellow frame the serene water view, while a wooden dock is visible in the background, inviting guests to enjoy the tranquil setting.

Home in Putnam Valley

Luxury Lake House Sauna 1h From NYC

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

4.99 out of 5 average rating, 131 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.

4.97 out of 5 average rating, 105 reviews

Apartment in Stony Point

Gorgeous Suite w/ Private Entrance

Welcome to your private upstairs retreat with its own private entrance and bathroom. This charming efficiency offers a queen bed for restful nights, plus a loveseat sleeper sofa perfect for an adult or two small children. Enjoy the convenience of a mini fridge, coffee maker, and microwave. Step outside your door to our porch sitting area with a grill. Thoughtfully set up to feel both private and inviting, it’s a peaceful space to relax, recharge, and feel right at home during your stay.

4.89 out of 5 average rating, 263 reviews

Apartment in Newburgh

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Farm stay in Fort Montgomery

A circle of bright orange Adirondack chairs surrounds a fire pit, which is highlighted by flickering flames. Lush green grass extends beneath the chairs, complemented by scattered yellow wildflowers. In the background, tall trees create a natural border under a clear blue sky.

4.93 out of 5 average rating, 282 reviews

Secluded mountain top horse property near W. Point

"Green acres is the place to be, farm living is the life for me!" This quaint little house trailer is located on a secluded horse farm in the beautiful Hudson Valley only 50 minutes from NYC and less than 10 mins from West Pt. situated on a mountain top. This private little space is a nature lovers paradise. Come, watch the horses from the front deck, enjoy fresh eggs in the morning, relax by the outdoor fire pit, star gaze & hike/explore forest trails right out the front door.

Apartment in Highland Falls

A two-story home is showcased with light-colored siding and vibrant red shutters. The entrance is marked by a white railing and steps leading to the front door. An American flag proudly stands on a flagpole in the front yard, bordered by a white picket fence.

4.97 out of 5 average rating, 122 reviews

Cozy West Point Hide Away and Cadet’s Get Away

Newly renovated basement space in a very quiet secluded neighborhood with a full kitchen, full size bathroom, Fast WiFi, Smart TV, Separate parking, walking distance to Hudson River, Main Street, Bear Mountain State Park, West Point Military Academy and several adventurous hiking trails. For those who like to shop we are located only 20 minutes to the Woodbury Commons and only a 45 minute drive to NYC. Also Stuart International Airport is only a short drive from here.

4.99 out of 5 average rating, 201 reviews

An open dining area features a wooden table surrounded by six dark chairs. A stylish light fixture hangs above, and a modern kitchen with white cabinetry and stainless steel appliances is visible in the background. Natural light filters through nearby windows.

Home in Highland Falls

Spacious, bright 5 bedroom house near West Point

Recently renovated 5 bedroom, 2 bathroom house located 4.3 miles from the Thayer Gate at historic West Point Military Academy. Located in the scenic Hudson Valley near hiking, fishing, Bear Mountain State Park and many historic sites.Woodbury Commons premium outlets are 20 minute drive. The house is comfortable with many upgrades- full oven and microwave, large fridge/freezer, USB ports .Come and see an Army game - and relax here afterwards!

Home in Cornwall-on-Hudson

A charming blue house features a welcoming front porch with steps leading up to the entrance. White shutters adorn the windows, and flower boxes add color. A flag is displayed in front, with a well-maintained lawn and greenery surrounding the property.

4.96 out of 5 average rating, 140 reviews

Charming Hudson Valley Home: Minutes to West Point

Located in the Lower Village of Cornwall on Hudson, 5 miles from West Point, 4 miles from Storm King Arts Center and minutes from amazing hiking trails. This charming house offers everything you need for a relaxing getaway. Spacious deck makes it the perfect spot for a relaxing evening outside. The beautiful Hudson Valley and this charming house can't wait to welcome you! **Home does not have a washer/dryer available

Popular amenities for Highland Falls outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.92 out of 5 average rating, 137 reviews

A spacious living room features a soft, light-colored couch and a small wooden coffee table. A flat-screen TV is mounted on the wall, while decorative shelves display greenery and art. Natural light streams in through windows dressed with sheer curtains.

Home in Newburgh

Lovely home in town of Newburgh

Home in Cornwall-on-Hudson

The exterior of a historic Gothic Victorian house displays a charming white façade with detailed gables and a covered front porch. Lush green lawns and trees surround the property, while a shaded outdoor seating area under a red umbrella adds to the inviting ambiance.

4.93 out of 5 average rating, 187 reviews

Cozy Riverfront Victorian in the Hudson Valley

5 out of 5 average rating, 217 reviews

A view of the exterior of the property is framed by lush greenery, featuring a stone wall with a potted plant. Beyond, expansive views of the lake and surrounding mountains are visible beneath a clear sky.

Home in Greenwood Lake

Panoramic Lakeviews & Garden Oasis

4.99 out of 5 average rating, 200 reviews

A spacious living area features large windows allowing ample natural light. A gray sectional couch is complemented by a mustard yellow chair and a round ottoman. Wooden flooring is contrasted by a blue area rug, adding warmth to the minimalist design.

Home in Newburgh

Balmville Mid-Century Gem & Work From Home Retreat

4.93 out of 5 average rating, 179 reviews

A Mediterranean style house is showcased against a backdrop of rolling hills and the Hudson River. The exterior features multiple windows, and a stone chimney rises from the roof. The expansive landscape is highlighted by autumn foliage, creating a vibrant setting.

Home in Garrison

Hudson Valley Mountaintop Riverview

4.99 out of 5 average rating, 175 reviews

A modern living area features a gray sofa with tufted seating, positioned near a wooden coffee table. Exposed wooden beams span the ceiling, while a cozy rattan chair adds warmth. Natural light streams through windows, creating a bright and airy ambiance.

Home in Beacon

NEW! Stylish Home in the Heart of Beacon

4.99 out of 5 average rating, 100 reviews

A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.

Home in Accord

Accord River House

Superhost

A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.

Home in Putnam Valley

4.94 out of 5 average rating, 128 reviews

Waterfront Lake House

Apartment rentals with outdoor seating

4.91 out of 5 average rating, 274 reviews

The log cabin is set amidst lush greenery and trees, featuring a sloped lawn that leads to the entrance. Solar panels adorn the roof, while diverse plant life and landscaping surround the home, creating a harmonious blend with nature.

Apartment in Philipstown

Foxglove Farm

4.88 out of 5 average rating, 235 reviews

A stained glass window adorns the top of the image, displaying intricate patterns in soft colors. Below, a large window frames a serene view of the Hudson River, with a cargo ship gliding across the water. Mountains rise gently in the distance under a pastel sky.

Apartment in Newburgh

Riversong on Hudson - Private Full 2nd Floor

Apartment in Cornwall-on-Hudson

A spacious living area is highlighted by a corner sectional sofa and a round marble coffee table. Soft, natural light filters through sheer white curtains, illuminating the warm wood floors. A dining space with a round table and modern chairs is visible in the background.

4.85 out of 5 average rating, 124 reviews

2-Bedroom in COH, near Newburgh & West Point

4.92 out of 5 average rating, 515 reviews

A bedroom features a spacious bed with neutral-toned bedding and decorative pillows. A small bedside table holds a clock, while a light fixture hangs above. The room is brightened by natural light streaming through a window with blinds, contrasting with the warm wooden floor and white walls.

Apartment in Newburgh

Riverview Rowhouse, a vintage modern home

4.99 out of 5 average rating, 180 reviews

The inviting interior features a well-lit living space with decorative wall sconces and a cozy seating area. A wooden table stands near a lush fern, while a TV is positioned on a mantel beneath framed artwork. Natural light enhances the space's warmth.

Apartment in Marlboro

Cozy Hudson Valley Retreat | 1800s Farmhouse

Superhost

Apartment in Beacon

4.9 out of 5 average rating, 720 reviews

Cozy Beacon Oasis

5 out of 5 average rating, 124 reviews

Apartment in Holmes

Top Side

4.94 out of 5 average rating, 175 reviews

A bright sleeping area features a spacious bed with white linens, complemented by two decorative pillows. A small side table with a lamp is positioned beside the bed. Light wood flooring and a window with dark curtains add warmth to the space. A chair and artwork are visible along the wall.

Apartment in Beacon

Walkable Studio with a Fire Pit

Condo rentals with outdoor seating

A spacious living area includes a cozy sitting area with large windows offering views of the surrounding landscape. A decorative fireplace adds warmth, while a small desk and chair provide a functional workspace. A dining table complements the layout, enhancing the room's versatility.

4.92 out of 5 average rating, 291 reviews

206 · Renovated Chic Premium 1 bdrm

A relaxing outdoor pool area features lounge chairs and red umbrellas, with a wooden sauna-like structure positioned nearby. Lush greenery surrounds the space, and a decorative stone wall enhances the rustic charm of the setting.

4.94 out of 5 average rating, 144 reviews

Sunsets at Mountain Creek! Walk to ski slopes!

4.75 out of 5 average rating, 124 reviews

Walk to Minerals weddings/winery/golf/bike/lakes

4.98 out of 5 average rating, 108 reviews

Cozy Luxury Mountain Retreat 2BR/2BA | Water Park

The living area features high ceilings and a spiral staircase leading to the loft. A blue couch faces a Smart TV, accompanied by a coffee table. A round dining table with blue placemats and four chairs is positioned nearby, offering an open view of the kitchen.

4.92 out of 5 average rating, 396 reviews

BRAND NEW! MODERN SlopeSide Condo, Golf, & Spa

A spacious living area is highlighted by a sectional sofa, positioned near large windows that welcome natural light. A dining table set for six is visible, complemented by a stylish chandelier above. A staircase with wooden steps adds a unique architectural element to the space.

4.99 out of 5 average rating, 146 reviews

Skiiis N Tees • Mountain Views, Cozy Vibes

A spacious living area is highlighted by a large sectional sofa adorned with decorative pillows. A round wooden coffee table sits in front, centered on a patterned area rug. A stylish electric fireplace is mounted on the wall, complemented by natural light from nearby windows.

4.9 out of 5 average rating, 109 reviews

Cozy Getaway by Mountain Creek, Minerals & Golf!

A serene bedroom space features a spacious bed adorned with cozy linens and decorative throw pillows. Geometric wall carvings in dark tones create an artistic backdrop, complemented by bedside lamps providing soft lighting. Natural light fills the room through a nearby window.