Holiday rentals with outdoor seating in Highland Falls

4.99 out of 5 average rating, 124 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.

5 out of 5 average rating, 100 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!

4.9 out of 5 average rating, 331 reviews

The interior of a wooden sauna is shown, featuring warm cedar walls and benches. A stove is located at the center, surrounded by two folding chairs and neatly rolled green towels. A wooden bucket sits in one corner, emphasizing the tranquil spa environment.

Flat in Cold Spring

HOT Sauna/COLD Plunge- Mountains-Hiking-NYC Trains

Your SPA - Cedar Barrel HOT SAUNA - Outdoor Cozy updated 1814 Cold Spring Village Classic-NATIONAL Historic Register Close to West Point & Beacon Guest Jack's comments "This apartment gave me the feel that I had my own place in a beautiful river town" Mountain Views - Sunny (12+ Windows) 3 Bedroom Modern Garden Apartment (850+SF) Cozy for 1 to 6 #1 Coffees & Teas Walk to Waterfalls, Hiking Trails, River Beaches, NYC trains Restaurants & cafes Outdoor living space in Garden - birds

4.83 out of 5 average rating, 285 reviews

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.

Flat in Highland Falls

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, 172 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

4.96 out of 5 average rating, 119 reviews

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

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

4.89 out of 5 average rating, 256 reviews

Flat 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!

4.94 out of 5 average rating, 162 reviews

A charming cabin with a red exterior is nestled among tall trees and autumn foliage. The building features multiple windows and a staircase leading to the entrance, while a rock border surrounds the lush ground cover and fallen leaves.

Cabin in Putnam Valley

Sweet, stylish cabin in the woods- hiking & more!

Only an hour north of NYC, but a world away! Adorable cabin in the woods offering stylish updated decor and beautiful natural surroundings. Brand new and completely renovated interior, but all the classic charm of the country. Trade in skyscrapers for tall trees in this sweet country escape that is near Fahnestock Park (surrounded by great hiking, skiing, etc) and 15m from the village of Cold Spring. Fully set up w/ wifi, Netflix & more! Quiet, considerate guests only please!

4.97 out of 5 average rating, 121 reviews

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.

Flat in Highland Falls

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.

Home in Cornwall-on-Hudson

A two-story house is situated on a quiet residential street, featuring a white exterior with a contrasting brick foundation. The entrance is framed by multiple windows, allowing natural light to illuminate the interior. A well-maintained yard with greenery surrounds the property.

4.86 out of 5 average rating, 151 reviews

Eclectic, Sleeps 5, Wsher/Dryer, Parking, Yard, AC

Clean 2-story house on a residential street/safe area Free on-off street parking Eat-in kitchen Dining room Living room-fold out ottoman Free washer-dryer in utility room 2 Internet TVs, WIFI Work area Large backyard, art supplies, games, books Fire pit Community Pool closed again. Close to West Point, Storm King, the Hudson, Woodbury Mall, hiking, restaurants, bars, shopping No river or mountain view directly from house. Airbnb threw that in.

4.99 out of 5 average rating, 198 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!

4.99 out of 5 average rating, 170 reviews

The restored a-frame stone cottage is nestled among trees, featuring a wooden deck and stone steps leading to the entrance. A propane grill is positioned on the deck, with a tranquil wooded backdrop showcasing the colors of nature.

Cottage in Pawling

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Popular amenities for outdoor seating rentals in Highland Falls

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

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, 184 reviews

Cozy Riverfront Victorian in the Hudson Valley

4.92 out of 5 average rating, 133 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

4.94 out of 5 average rating, 282 reviews

Home in Wappingers Falls

Tranquil Tree-House on the beautiful Hudson River

4.96 out of 5 average rating, 167 reviews

An open living space features a Foster Leather sectional sofa positioned around a central coffee table. Natural light streams in from a large window, illuminating the wood-burning stove nearby. A cozy area rug adds texture to the floor, creating an inviting atmosphere.

Home in Gardiner

Mindful Escape: Theater, Trails, Wood Stove

4.97 out of 5 average rating, 144 reviews

A cozy bedroom features a spacious bed with a light-colored coverlet, flanked by dark lamps on wooden nightstands. Soft, natural wood beams are visible on the sloped ceiling, while a green area rug adds a touch of color to the wood floor.

Home in Kerhonkson

The Nest at Minnewaska

5 out of 5 average rating, 216 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

Spectacular Lake Views from Every Room & Garden

4.99 out of 5 average rating, 196 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

4.99 out of 5 average rating, 127 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

Apartment rentals with outdoor seating

A spacious deck is captured in the image, featuring two green wicker chairs arranged on a wooden floor. The open railings provide a view of surrounding trees and a clear sky, creating a relaxed outdoor setting for guests to enjoy.

4.97 out of 5 average rating, 170 reviews

Beacon Bird's eye view! Close to Main St & Train

4.9 out of 5 average rating, 269 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.

Flat in Philipstown

Foxglove Farm

4.98 out of 5 average rating, 380 reviews

A cozy bedroom corner is featured, showcasing a spacious bed with neatly arranged pillows and blankets. A 50" 4K TV displays a calming fireplace scene, illuminating the room softly. The entryway to the bathroom is visible in the background.

Flat in Croton-on-Hudson

Luxury 2bd⭐Comfort+Style⭐

A spacious kitchen and dining area feature light wood cabinetry and modern stainless steel appliances. A wooden dining table is complemented by white chairs, and a window seat provides natural light. Decorative elements include a bowl of fruit at the center of the table.

4.85 out of 5 average rating, 763 reviews

Top Floor 2BR

4.85 out of 5 average rating, 195 reviews

A modern kitchen area features sleek blue cabinetry complemented by a stainless steel refrigerator. A white countertop provides workspace above a stainless sink, with a dish rack nearby. The floor is adorned with a textured gray surface, contributing to the kitchen's contemporary feel.

Flat in Nelsonville

Wooded stream side Retreat

4.99 out of 5 average rating, 219 reviews

Private Apt 2 Blocks MainSt/Roundhouse/MT/Maribeau

Flat 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, 122 reviews

2-Bedroom in COH, near Newburgh & West Point

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.

4.93 out of 5 average rating, 167 reviews

Walkable Studio with a Fire Pit

Apartment rentals with outdoor seating

A spacious living area features a comfortable sofa alongside two accent chairs. A wooden coffee table sits in the center, with a dining area visible in the background, adorned with a large pendant light. A piece of framed artwork hangs above the seating.

4.92 out of 5 average rating, 116 reviews

Premium New 1bd Sunset Balcony 3rd flr

An illuminated salt-water pool reflects soft light at night, surrounded by a well-maintained patio. The backdrop features a multi-story building with balconies and warm lights glowing from the windows, creating a serene atmosphere.

4.88 out of 5 average rating, 141 reviews

Valley Overlook @ Mtn Creek Resort Park & Play

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

4.99 out of 5 average rating, 103 reviews

Luxurious Cozy Mountain Retreat 2BR/2BA – Ski/Spa

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, 390 reviews

BRAND NEW! MODERN SlopeSide Condo, Golf, & Spa

A spacious living area showcases a large sectional sofa and a coffee table on a patterned rug. Natural light fills the space through expansive glass doors that lead to an outdoor area. A spiral staircase leads to an upper level, while a dining area features a stylish chandelier.

4.99 out of 5 average rating, 142 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.