Vacation rentals in Highland Falls

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Quick stats about vacation rentals in Highland Falls

  • Total vacation rentals

    Explore 60 vacation rentals in Highland Falls

  • Nightly prices starting at

    Highland Falls vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 3,690 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Highland Falls vacation rentals include wi-fi access

  • Popular amenities for guests

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

  • 4.9 Average rating

    Highland Falls stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Highland Falls

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Home in Highland Falls
4.97 out of 5 average rating, 121 reviews

Ultimate Walking Access to Thayer Gate USMA

Stay an extra day on us! Book 4 nights and get the 5th night free at this beautiful farmhouse. Enjoy the ultimate walking access to Thayer Gate and immerse yourself in the West Point experience. Hosted by a ‘23 Old Grad Mom, our home features a kitchen with granite counters, dining for 10, a 75” SmartTV, and a great backyard for entertaining. Relax in cold AC near the Academy. No smoking or pets. No exceptions/loss of deposit. Book your Army getaway today! No smoking or pets or loss of deposit.

Top guest favorite
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
5 out of 5 average rating, 102 reviews

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!

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, 120 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
The exterior of a two-story house is presented against a colorful sunset sky, with hues of pink and orange blending together. A well-maintained lawn extends in front, while steps lead to the entrance, framed by tall trees and utility lines.
Guest suite in Highland Falls
5 out of 5 average rating, 65 reviews

Quiet, Cozy, Private Suite ~1/2 mile to West Point

The neighborhood is so quiet w/ beautiful views everywhere you look. It's a private suite, w/ private entrance & bathroom, microwave, toaster oven, mini-fridge, & of course, a coffee maker! Extra living space w/ a couch, desk & smart TV. Work out in the morning or watch TV at night. Only ~1/2 mile to West Point, so Main Street (food/drink) & Thayer Gate are in walking distance. Perfect for visiting anyone or attending an event at West Point. Quaint towns, restaurants, hiking in all directions

Guest favorite
A comfortable loveseat is presented in a muted grey fabric, featuring tufted details and two soft pillows. A textured cushion adds a touch of warmth. The background showcases a smooth, light-toned flooring that complements the modern aesthetic of the space.
Apartment in Highland Falls
4.86 out of 5 average rating, 35 reviews

West Point Rest Stop

Just walking distance of public parking in Highland Falls. We are mere minutes away from Thayer Gates and conveniently situated across from the West Point Museum on Main Street. From our location, there are numerous options available for foot travel. Additionally,we are within a short driving distance of numerous local attractions, including Bear Mountain, Legoland, Woodbury Commons, Catskill Resorts Casino, and numerous museums, hiking trails, dining establishments, and shopping opportunity

Top guest favorite
The exterior of a historic home is showcased, featuring a covered wrap-around porch adorned with patriotic bunting and seating. The interior displays a modern kitchen with granite countertops and stainless-steel appliances, a cozy living room with a comfortable seating area, and a stylish dining space set for six.
Home in Highland Falls
5 out of 5 average rating, 96 reviews

Top-Rated West Point 3 Bed 2 Bath Walk to Thayer

Book 4 nights and get the 5th night free! Welcome to the West Point Grad Mom House — Whether you’re visiting your Plebe, Yearling, Cow or Firstie our home was designed with West Point families in mind just steps from Thayer Gate. Why families love staying here: • Walk to Thayer Gate, Main Street • Easy access to West Point • Spacious gathering areas • Historic charm combined with modern comfort • Thoughtful touches from a fellow Grad Mom who understands how special these visits are

Guest favorite
Apartment in Newburgh
4.89 out of 5 average rating, 261 reviews

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!

Top guest favorite
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.
Apartment in Highland Falls
4.97 out of 5 average rating, 121 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.

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, 200 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!

Guest favorite
The living room features a combination of a black sofa and a light gray couch, adorned with red accent pillows. A wooden coffee table is positioned in the center, and light from a nearby window illuminates the space, complemented by a ceiling fan and wall-mounted television.
Home in Highland Falls
4.82 out of 5 average rating, 132 reviews

Lovely 3BR Home with parking-Walk to WP Gate!

Walk to West Point! Enjoy the Hudson Valley. Bring the whole family to this great place with lots of room for fun. Cozy up in our spacious living room while dinner is cooking in the fully equipped kitchen. The back deck is perfect for morning coffee, unwinding in the evening with a glass of wine or a family BBQ. You will find everything you need for work or play here in the heart of Highland Falls, New York. Looking forward to having you!

Guest favorite
A comfortable sleeping area features a metal frame bed with white bedding. Framed black-and-white photographs adorn the wall above the bed. A small bedside table holds a lamp. Partially covered windows allow natural light to fill the space, and a door leads outside.
Apartment in Newburgh
4.97 out of 5 average rating, 113 reviews

Historic one-bedroom apartment

Welcome! Our home is a Federal period row house built in 1836, designed by Thornton Niven. It is one of five homes together known as Quality Row. Our home was the first residential building in Newburgh to be electrified by Thomas Edison, and Edison himself was a guest here while setting up the power station on Montgomery Street to electrify Newburgh.

Guest favorite
The exterior of the renovated home is framed by lush, green hedges. A covered front porch features a light blue seating set with two chairs and a small table. Freshly painted siding complements the welcoming entrance, creating an inviting first impression.
Home in Highland Falls
4.97 out of 5 average rating, 64 reviews

Highland Falls Home - 1/2 Mile to West Point

Renovated Home Within walking distance (.5 miles) of West Point. Very neat and clean. Located in the scenic Hudson Valley near hiking, fishing, Bear Mountain State Park, and many historic sites. Come and see an Army game - and relax here afterward!

Popular amenities for Highland Falls vacation rentals

When is the best time to visit Highland Falls?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 988ﺩ.ﺇ 988ﺩ.ﺇ 808ﺩ.ﺇ 918ﺩ.ﺇ 999ﺩ.ﺇ 1,032ﺩ.ﺇ 936ﺩ.ﺇ 951ﺩ.ﺇ 940ﺩ.ﺇ 1,025ﺩ.ﺇ 1,102ﺩ.ﺇ 970
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

Frequently Asked Questions

  • What are the best places to stay in Highland Falls?

    Stays around Highland Falls village allow you to explore charming streets, local eateries, and nearby nature. Homes near the riverside and in quiet residential areas are often recommended for both relaxation and accessibility.

  • What are the best things to do in Highland Falls with kids?

    Families often explore parks and riverside picnic spots or visit local playgrounds. Nature walks, seasonal community events, and nearby educational attractions create opportunities for fun and learning.

  • What are some of the best things to do in Highland Falls?

    Explore the scenic Hudson River waterfront and enjoy local shops around the village. Highland Falls has hiking trails, historic sites, and easy access to outdoor adventure and nearby cultural spots.

  • How is the weather in Highland Falls?

    Highland Falls has cold winters around 16–35°F (-9–1°C), with snow likely, and warm summers near 59–82°F (15–28°C). Spring and fall bring mild, changeable weather, often paired with colorful foliage and outdoor activity.

  • When is the best time to visit Highland Falls?

    Late spring and autumn are often recommended, when mild weather and colorful foliage make outdoor activities popular. Summer attracts visitors for community events and riverside gatherings, while winter brings a quieter pace and the possibility of snow.

  • What are the best places to visit in Highland Falls?

    Highland Falls has a lively village center, scenic riverfront areas, and is near the United States Military Academy campus, which often draws history enthusiasts. Local parks and historic markers highlight the region's stories and natural charm.

  • What are some hiking trails in Highland Falls?

    Highland Falls has woodland trails and riverside paths ideal for hiking and nature walks. Local parks and preserves provide trails for a range of ability levels, with seasonal views of the river and hills.

  • What are some family activities we can do in Highland Falls?

    Families frequently explore playgrounds, hike gentle trails, and participate in local arts workshops. Seasonal events and riverside picnics make Highland Falls a welcoming spot for all ages.

  • What are some of the best day trip ideas from Highland Falls?

    Explore arts and gardens in surrounding towns, visit nature preserves, or discover historic sites in the Hudson Valley. The area around Highland Falls frequently draws visitors for outdoor activities and cultural experiences.

  • Are there any pet friendly accommodations available in Highland Falls?

    Many vacation rentals in Highland Falls welcome pets, especially in residential areas near parks and walking paths. Some hosts provide extra amenities for pets, such as a fenced yard or pet bowls.

  • What are some local tips for visiting Highland Falls?

    Locals suggest exploring the village early to enjoy peaceful streets and fresh bakery treats. If hiking, check trail conditions and bring bug spray; autumn colors around Highland Falls are frequently suggested for photography.

  • What is Highland Falls known for?

    Highland Falls is known for its riverside scenery, historic connection to the United States Military Academy, and access to hiking in nearby hills. The village atmosphere and local events contribute to its distinct character.

  • What are the best hidden gems to explore in Highland Falls?

    Wander lesser-known woodland trails and discover tranquil spots along the riverbanks. Small galleries or historic plaques around the village often share stories of the area’s past and local artists.

  • What are the best foods to try in Highland Falls?

    Explore locally rooted flavors, including American classics, fresh baked goods, and seasonal farm produce. The area is known for its casual cafes, family diners, and small eateries serving diverse cuisine.

  • What should I bring for a trip to Highland Falls?

    Pack comfortable walking shoes, layered clothing for changing temperatures, and a rain jacket. A reusable water bottle and sunscreen are helpful for outdoor activities, especially during warmer months.

  • What is the nightlife in Highland Falls like?

    Nightlife in Highland Falls has a relaxed vibe, centering on local pubs, casual eateries, and occasional live performances. Evening strolls by the river and nearby taverns create a warm, welcoming atmosphere.

  • What are the most popular events or festivals in Highland Falls?

    Highland Falls features community celebrations, summer outdoor concerts, and seasonal festivals often tied to national holidays like Memorial Day or Independence Day. Local fairs and arts events in late spring and early fall draw both residents and visitors.

  • Are there family friendly vacation rentals in Highland Falls?

    Highland Falls has a variety of vacation rentals suitable for families, including spacious homes and apartments. Many accommodations feature amenities like kitchens, extra bedrooms, and easy access to parks and local attractions.

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