
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.

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.

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!

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!

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

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-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

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!

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.

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!

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!

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.

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
Other great vacation rentals in Highland Falls

Highland Falls Home away from Home. Walk to Thayer

Highlands Retreat

Old Grad House, within Cadet Walking Privileges

Cozy House 3 Blocks From West Pt

Delightful Home!

The Cottage

Discover Nature’s Glory! Perfect Family Home

Lovely 2nd FL Apt Walking Distance to West Point!
When is the best time to visit Highland Falls?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 988 | ﺩ.ﺇ 988 | ﺩ.ﺇ 808 | ﺩ.ﺇ 918 | ﺩ.ﺇ 999 | ﺩ.ﺇ 1,032 | ﺩ.ﺇ 936 | ﺩ.ﺇ 951 | ﺩ.ﺇ 940 | ﺩ.ﺇ 1,025 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 970 |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°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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