Holiday rentals in Highland Falls
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Quick stats about holiday rentals in Highland Falls
Total holiday rentals
Explore 60 holiday rentals in Highland Falls
Nightly prices starting at
Highland Falls holiday rentals start at $65 SGD per night before taxes and fees
Verified guest reviews
Over 3,690 verified reviews to help you choose
Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 of Highland Falls holiday rentals include wifi 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 holiday rentals in Highland Falls
Guests agree: these stays are highly rated for location, cleanliness and more.
Quaint Apartment in Cornwall on Hudson
Looking for a weekend getaway? Come experience this centrally-located apartment in the quaint village of Cornwall-on-Hudson. Step outside to find river views, enjoy miles of hiking trails, Hudson River picnics and kayaking that start right up the road. Just minutes to West Point, the Storm King Art Center, Mount Beacon and Woodbury Commons and still in walking distance to shops, restaurants, and parks. We’re excited to make this your favorite place to stay while visiting the Hudson Valley area.
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!
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
Lovely 2nd FL Apt Walking Distance to West Point!
Welcome To The Heart Of West Point. Beautifully Furnished Apartment. Located Steps Away from West Point. Walking Distance to Restaurants, & The Best Landmarks The Town Has To Offer. We Are Minutes Away From Hiking,Swimming, Fishing, & Much More! We are Ideally Located Near Bear Mountain State Park, Woodbury Commons & More! Apartment Includes 2 Full Size Bed, 1 Roll out Twin Bed. Comfortable Couches, Smart Tv, Wifi, & Much More. NO Parties. Family Living on 1st Floor Apartment.
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-Rated West Point 3 Bed 2 Bath Walk to Thayer
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
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!
Hudson Haven
Welcome to our peaceful, private in-law apartment just minutes from West Point. Originally designed for my mom’s future independence, it’s now the perfect guest retreat—quiet, cozy, and full of charm. You’ll have your own entrance, off-street parking, and a sunny porch to enjoy your morning coffee. The apartment is filled with natural light, thoughtful touches, and mountain views, all nestled in a quiet neighborhood
Secluded overlook cottage near West Point
This quaint little house trailer is located on a secluded horse farm in the beautiful Hudson Valley only 50 minutes from NYC and less than 10 minutes from West Pt. Situated on a mountain top, this private little space is a nature lovers paradise. Come, recline on the new outdoor deck, relax by the fire pit and hike/explore the forest trails right out the front door.
Delightful Home!
Experience a thrilling gateway from the bustling energy of New York City in this delightful home! Centrally-located, just a short 5-minutes walk to West Point Military Academy and Thayer, and a mere 5.2 miles to the breathtaking Bear Mountain State Park. Adventures await right at your doorstep!
Popular amenities for Highland Falls holiday rentals
Other great holiday rentals in Highland Falls
Highland Falls Home away from Home. Walk to Thayer
Highlands Retreat
West Point Family Retreat 5 min walk to Thayer
Old Grad House, within Cadet Walking Privileges
Cozy House 3 Blocks From West Pt
Local Artist Inspired | Walk to WestPoint+King Bed
West Point Apartment/Highland Falls NY
West Point Hudson Valley Getaway
When is the best time to visit Highland Falls?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $348 SGD | $348 SGD | $285 SGD | $324 SGD | $352 SGD | $364 SGD | $330 SGD | $335 SGD | $331 SGD | $361 SGD | $388 SGD | $342 SGD |
| 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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- Times Square
- MetLife Stadium
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