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House vacation rentals in Highland Falls

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Top-rated house rentals in Highland Falls

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Top guest favorite

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.

4.99 out of 5 average rating, 144 reviews

NEW! Stylish Home in the Heart of Beacon

This Scandinavian style home in the heart of Beacon is bright, airy and modern with beautifully-restored architectural details. Located on a quaint street in the best part of town just steps away from the Roundhouse and Main Street. Enjoy the brewery, bars, restaurants, shops, galleries, and so much more - all within walking distance. Every piece of furniture and decor was handpicked to provide you the perfect designer-quality getaway, focusing on natural simplicity with contemporary luxuries.

A spacious outdoor area features a sleek gunite pool surrounded by lounge chairs and umbrellas. Lush greenery and blooming flowers provide a serene backdrop, while full views of the Hudson River and distant mountains contribute to the tranquil atmosphere.

Home in Newburgh

4.98 out of 5 average rating, 118 reviews

Hudson River House

Friends and family will be wowed when gathering at this spacious mid-century riverfront home. There’s a beautiful new gunite pool, hot tub, large patio, screened floating porch, and spacious decks for barbecuing and dining. Interiors feature 2 fireplaces, 2 living spaces with large TVs, fully-equipped kitchen, game room, exercise area, piano, home office, and lots of space to spread out both inside and outside. All of it looks out to the Hudson River where you may spy bald eagles nesting nearby.

Top guest favorite

A two-story white house is framed by lush green trees. The front porch features red rocking chairs and hanging flower baskets. An American flag is displayed on the porch. A pathway leads to the entrance, which is highlighted by white railings and steps.

Home in Cornwall-on-Hudson

4.99 out of 5 average rating, 108 reviews

Your West Point Academy Home Away from Home

Make yourselves at home in this lovely, privately-owned residence as you attend West Point Academy events and tour scenic Hudson Valley. Build in 1900 and renovated in 2019, this house combines historic charm (original wood floors) with modern conveniences. The home's location is a twelve-minute drive to West Point's Washington Gate and within walking distance to the restaurants and shops of Cornwall. Enjoy 4th of July fireworks and weekly summer concerts with ease relaxing on the front porch!

Top guest favorite

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

4.99 out of 5 average rating, 121 reviews

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

A charming cottage is framed by trees, with a welcoming yellow door nestled among the greenery. A stone pathway leads to the entrance, bordered by well-maintained grass. Natural light filters through the surrounding foliage, enhancing the peaceful ambiance of the setting.

Home in Cold Spring

4.95 out of 5 average rating, 132 reviews

Peaceful Yellow Door Cottage

Yellow Door Cottage is a quiet family getaway nestled in the woods, but close to the historic Village of Cold Spring. Large backyard, ideal for afternoon lunch on the deck or an evening around the fire. Located on a lovely country road, great for walking and biking. 3 comfy bedrooms with linens supplied. Wi-Fi, TVs, washer/dryer, close to amazing hikes and the beautiful Hudson River! Rent alone or pair with my cottage next door: Cheerful Private 3 Bedroom Cottage in Cold Spring on Airbnb.

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.

Home in Cornwall-on-Hudson

4.92 out of 5 average rating, 169 reviews

Cozy Riverfront Victorian in the Hudson Valley

Wake up to stunning views of the Hudson River in this huge, immaculately clean, & beautifully designed historic home. Welcome to Sparrow House, our one-of-a-kind 1859 Gothic Victorian in the Hudson Valley. Only 80 minutes from NYC, 19 minutes away from the Beacon stop on the Hudson line/Metro-North, and 13 minutes from the Salisbury Mills/Cornwall Stop on the Port Jervis line/NJ Transit. The house is spacious, has exquisite light, and river and mountain views from nearly every room.

A charming two-story house is featured with a light yellow facade and white trim. A welcoming front porch with a bench overlooks the neatly landscaped yard, filled with greenery and flower beds. The inviting entrance is flanked by large windows and decorative shutters.

Home in Newburgh

4.86 out of 5 average rating, 105 reviews

Lady Montgomery

Enjoy this trendy and comfortable home overlooking the Hudson river. Lady Montgomery is set in the perfect family-friendly neighborhood, walking distance to the bridge and Newburgh waterfront. Perfect for friends and couples who want to explore all the Hudson Valley has to offer like shopping, hiking or dining. Equipped with an outdoor patio, fire pit and two bikes to help you explore the surrounding areas. Everyone will enjoy their time in this comfortable artistic home.

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.

Home in Cornwall-on-Hudson

4.87 out of 5 average rating, 133 reviews

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

This is a 2-story house-quiet residential street-safe town. Clean, eat-in kitchen, dining room, 2 twins, one queen, fold out bed in Living Room, shower/tub, washer/dryer, dedicated work area, Internet TV and ROKU 2nd floor, art supplies, large backyard, sml bbq, fire pit, games, kid-friendly. Free on/off-street parking. Close to Storm King, the Hudson, Woodbury Mall, West Point, hiking, restaurants, bars, malls. Town pool easy walking distance. No river or mountain view.

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

4.99 out of 5 average rating, 165 reviews

Balmville Mid-Century Gem & Work From Home Retreat

Gather with friends and family or enjoy a work from home getaway in this mid century gem, located in the lovely hamlet of Balmville. This section of the Hudson River Valley is known for its well-maintained historic homes, river views, and vibrant culture. Enjoy dinner and cocktails in the city of Newburgh just 1.5 miles away, or cross the bridge to Beacon (just 5 miles away) and enjoy all Main Street has to offer. Hike Mount Beacon, Breakneck Ridge, and more.

Top guest favorite

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

4.99 out of 5 average rating, 175 reviews

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!

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.

Home in Cornwall-on-Hudson

4.96 out of 5 average rating, 126 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

The exterior of a split-level home is shown, featuring a mix of brick and siding. A set of wooden stairs leads to a front deck with a patio umbrella. Two small shrubs are planted near the entrance, and a driveway is visible in the foreground.

Home in Highland Falls

4.99 out of 5 average rating, 111 reviews

Cozy 4 Bed 2 Bath Home 1/4 mile from West Point

Split level floor plan featuring 4 spacious, bright bedrooms and 2 full baths. Newly renovated home with large deck for entertaining. Sleeps 10 with room to spare. Quiet end street 1/4 mile from Thayer Hotel at USMA. Walking distance to several restaurants. Amenities include: Satellite TV/WiFi/Washer-Dryer/Dishwasher/Outdoor grill.

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Popular amenities for Highland Falls house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.

Home in Stormville

4.94 out of 5 average rating, 190 reviews

Private Hudson Valley Country Retreat

Top guest favorite

Home in New Paltz

4.98 out of 5 average rating, 499 reviews

midcentury mod * HOT TUB * walk out trail 2 mohonk

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4.88 out of 5 average rating, 152 reviews

4Br Mountain Brook House on 130 acres w/ trails

A spacious outdoor pool is surrounded by a stone patio, nestled within a serene environment of tall trees. The pool features a diving board and is complemented by nearby planters. A main house can be seen in the background, enhancing the tranquil setting.

Home in Stamford

4.95 out of 5 average rating, 256 reviews

Midcentury Modern ZenHouse Sculptor Studio

An aerial view captures a stylish retreat surrounded by lush greenery. A wooden deck outlines a rectangular saltwater pool, accompanied by lounge chairs and large umbrellas. A shaded seating area is positioned nearby, promoting outdoor relaxation.

Home in Kerhonkson

4.93 out of 5 average rating, 126 reviews

Modern Lux 5-Bed, Pool Open! Dogs Welcome

Top guest favorite

A serene outdoor space features a heated saltwater pool surrounded by well-maintained grass. Lounge chairs are positioned along the pool's edge under the shade of a large tree, creating a peaceful area for relaxation. The property is bordered by a wooden fence and offers expansive views of the surrounding landscape.

Home in Pound Ridge

5 out of 5 average rating, 168 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

The spacious backyard features a well-maintained in-ground pool surrounded by lush green grass. Comfortable lounge chairs are positioned on the deck and by the pool. A slide is present for added fun, while the home is partially visible with an elevated deck overlooking the area.

4.92 out of 5 average rating, 139 reviews

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

The exterior of a Victorian-style farmhouse is visible, surrounded by lush greenery. A wraparound porch adds architectural interest, adorned with white railings. The sloped roof and multiple gables characterize the charming structure. Pathways lead through the well-maintained gardens, inviting exploration of the natural surroundings.

Home in Grahamsville

4.89 out of 5 average rating, 102 reviews

Spacious Catskills Farmhouse w/ In-Ground Pool!

Weekly house rentals

A spacious living area features a large brown sectional sofa, complemented by a round coffee table. A patterned area rug adds color to the tiled floor. Natural light enters through large windows, while a spiral staircase leads to an upper level.

Home in Fort Montgomery

5 out of 5 average rating, 23 reviews

Modern 4 bedroom home near West Point & Bear Mt.

Top guest favorite

The living room features a stone fireplace and a large wall-mounted television. Two blue armchairs are positioned next to a light-colored coffee table. A staircase with wooden steps leads to the upper floor, and artwork adorns the walls.

Home in Highland Falls

5 out of 5 average rating, 11 reviews

West Point Family Retreat 5 min walk to Thayer

Top guest favorite

The exterior of a two-story blue house is highlighted by white trim and black shutters. A small porch with steps leads to the entrance, flanked by neatly trimmed shrubs. A flag pole stands to the right, and a pathway of stones cuts through the grassy front yard.

Home in Highland Falls

5 out of 5 average rating, 16 reviews

Old Grad House, 850ft from Thayer Gate

A two-story house features a green exterior with a prominent red front door. Solar panels are arranged on the roof, and a welcoming porch with white railings invites relaxation. The backdrop showcases a serene landscape with bare trees, illuminated by a soft sunset sky.

Home in Cornwall

4.97 out of 5 average rating, 32 reviews

Cozy Cornwall Retreat Near Hudson Valley

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

4.97 out of 5 average rating, 89 reviews

West Point Mountain House

Top guest favorite

An open-concept living space features high wooden beam ceilings and a stone fireplace. Large windows provide ample natural light and scenic views of the lake. A staircase leads to an upper level, while a cozy seating area is arranged nearby, emphasizing relaxed living.

Home in Putnam Valley

5 out of 5 average rating, 17 reviews

Dr. Ruth’s Serene Lake Retreat

A spacious living area features an elegant chandelier hanging from a wooden beam ceiling. A white chaise lounge and a blue armchair are positioned around a wooden coffee table. Warm light enters through windows, illuminating the colorful area rug that covers the hardwood floor.

Home in Highland Falls

4.97 out of 5 average rating, 62 reviews

West Point Hudson Valley Getaway

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

4.97 out of 5 average rating, 78 reviews

Waterfront Lake House

Private house rentals

Top guest favorite

A sunlit sun room features large windows offering scenic lake views and a warm wooden ceiling. A cozy, circular seating area complements a central wooden table. Nearby, a dining table with black chairs sits atop a modern area rug, enriching the space's inviting ambiance.

Home in Vernon Township

5 out of 5 average rating, 76 reviews

Private Island + Lakefront Home

Top guest favorite

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

4.96 out of 5 average rating, 71 reviews

Mindful Escape: Theater, Trails, Wood Stove

Top guest favorite

The living room features two navy blue sofas positioned across from each other, creating a welcoming conversation area. A glass coffee table is centered on a light-colored carpet. Natural light filters through sheer curtains, highlighting views of the surrounding greenery.

Home in Cornwall

4.98 out of 5 average rating, 47 reviews

Sunset House: near West Point, Hiking & Woodbury

A single-story home is presented with a welcoming front porch featuring white columns and a light grey exterior. The porch includes a wooden step entry leading to the front door, surrounded by lush greenery and a gated fence, providing a cozy, private outdoor space.

Home in Newburgh

4.88 out of 5 average rating, 32 reviews

Margaret's Heart

Top guest favorite

A bright living area features a soft blue sofa paired with a wooden armchair. Natural light streams through two windows adorned with sheer curtains, illuminating a side table and framed artwork on the wall. An inviting atmosphere is created by decorative cushions and polished wooden flooring.

4.94 out of 5 average rating, 33 reviews

The Gîte - Hudson Valley Retreat

A spacious backyard features a circular arrangement of red Adirondack chairs surrounding a stone fire pit. The house stands in the background, with large windows providing a view of the surrounding trees and greenery, inviting outdoor gatherings and relaxation.

Home in Putnam Valley

4.94 out of 5 average rating, 70 reviews

Chic Cozy Upstate Cabin Just 1 Hr From NYC!

Top guest favorite

A stone patio is shown with six colorful chairs arranged around a fire pit. In the background, trees and a trampoline are visible, contributing to a serene outdoor setting, ideal for gathering and relaxation.

Home in Mohegan Lake

4.95 out of 5 average rating, 57 reviews

A nice place to getaway

A light-filled living area showcases a comfortable sectional sofa adorned with decorative cushions. A wooden coffee table sits in the center, complemented by a small decorative item. Sheer curtains frame the window, allowing natural light to illuminate the space.

Home in Newburgh

5 out of 5 average rating, 5 reviews

Charming Apartment in Newburgh

Quick stats about house rentals in Highland Falls

Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore