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 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, 142 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

Superhost
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, 119 reviews

Lady Montgomery

Enjoy our trendy and comfortable home overlooking the Hudson river. Lady Montgomery is set in the perfect family-friendly neighborhood, walking distance to the bridge trail to Beacon and Newburgh waterfront. Perfect for friends and couples who want to explore all that the Hudson Valley has to offer like shopping, hiking or dining. Equipped with an outdoor patio, fireplace, fire pit and 2 bikes to help you explore the area. Everyone will enjoy their time in this comfortable artistic home!

Top guest favorite
A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.
Home in Cold Spring
4.95 out of 5 average rating, 175 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Top guest favorite
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 Sterling Forest
5 out of 5 average rating, 203 reviews

Spectacular Lake Views from Every Room & Garden

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

Guest favorite
A circular stone patio surrounds a central fire pit, featuring six red Adirondack chairs. The modern house with a welcoming entrance is partially obscured by lush green trees in the background, creating a natural and serene environment.
Home in Montgomery
4.96 out of 5 average rating, 117 reviews

Modern Woodland Retreat, Hudson Valley & Catskills

A dreamy forest retreat wrapped in trees and good light—perfect for couples or families. Lounge on the deck, sip wine by the fire pit, or sleep in under plush bedding. Inside, you’ll find a fully stocked kitchen, organic toiletries, toys, books, and baby gear—all thoughtfully chosen for comfort and ease. Minutes from Beacon, New Paltz, and Harriman State Park for hikes, river towns, swimming holes, farmers markets, and slow mornings that stretch into golden afternoons.

Top guest favorite
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, 181 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
A charming two-story house features a combination of red siding and stone accents. A welcoming porch with white railings leads to the front door. Lush greenery surrounds the entrance, enhancing the inviting exterior. Nearby, a well-maintained lawn adds to the home's appeal.
Home in Newburgh
4.99 out of 5 average rating, 131 reviews

The Little Red House

Located in a quiet neighborhood just off the Hudson River, yet only a 10 min drive from the bustling town of Beacon and within walking distance to the Newburgh action where you will find restaurants, coffee shops, galleries local shopping, and nightlife. With countless hiking spots, farms, breweries, and wineries, your stay in Hudson Valley will be memorable. The house was also a filming & staging location for the movie “Adults” starring Michael Cera

Superhost
An aerial view captures a spacious lakefront property surrounded by lush greenery. Trees frame the yard, which gently slopes toward the water. The exterior of the house is clad in light gray, with multiple windows reflecting the natural surroundings. A patio area is visible near the water's edge.
Home in Putnam Valley
4.92 out of 5 average rating, 111 reviews

Crystal Wave LakeHouse

Make some memories at this renovated, family-friendly Lakefront Oasis! Water activities on your own Peninsula with Lake Frontage on 3 Sides of the Property! Views of the Lake from Almost Every Window! Included is an extra 600 sq ft cottage that has been completely renovated for your enjoyment with a pool table. Utilized as a gaming room & yoga studio! There is a pullout sofa as well for extra guests with a bathroom a few steps away in the main house!

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, 188 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!

Top guest favorite
Home in Wappingers Falls
4.94 out of 5 average rating, 262 reviews

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. I look forward to hosting you. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door.

Guest favorite
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
4.92 out of 5 average rating, 120 reviews

Lovely home in town of Newburgh

PLEASE READ FULL DESCRIPTION PRIOR TO BOOKING! Welcome to our cozy and stylish home located in the town of Newburgh. This modern space offers comfort and convenience with a fully equipped kitchen, comfortable beds, washer & dryer, and a central location close to shops and restaurants. Perfect for both business and leisure travelers.

Top guest favorite
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, 116 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.

Popular amenities for Highland Falls house rentals

When is the best time to visit Highland Falls?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ933ﺩ.ﺇ940ﺩ.ﺇ826ﺩ.ﺇ1,072ﺩ.ﺇ1,219ﺩ.ﺇ1,127ﺩ.ﺇ1,102ﺩ.ﺇ1,124ﺩ.ﺇ1,083ﺩ.ﺇ1,175ﺩ.ﺇ1,337ﺩ.ﺇ1,069
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Quick stats about house rentals in Highland Falls

  • Total vacation rentals

    Explore 40 vacation rentals in Highland Falls

  • Nightly prices starting at

    Highland Falls vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 1,800 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Highland Falls vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Highland Falls rentals

  • 4.8 Average rating

    Highland Falls stays are highly rated by guests—averaging 4.8 out of 5!

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