Holiday houses 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 $87 NZD per night before taxes and fees
Verified guest reviews
Over 3,900 verified reviews to help you choose
Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wi-Fi availability
60 of Highland Falls holiday 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 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.
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Ranch in the Woods | A Peaceful Designer Retreat
Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.
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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!
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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
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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.
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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
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Cozy House 3 Blocks From West Pt
Welcome to this thoughtfully remodeled Historic 1890s home, just steps away from West Point's Thayer Gate. The house is conveniently situated right by Thayer Gate (3 blocks) where there are shuttles to all events and destinations. Steps away (1 block) from the restaurants on Main street and the West Point visiting center and Museum (3 blocks). 10 Mins to Bear Mountain State Park 15 Mins to Storm King Art Center 20 Mins to Woodbury Commons
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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!
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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!
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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.
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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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The Cottage
Quiet neighborhood, walking distance to town and Academy. Perfect for family visiting students. Also a quick getaway from NYC, 1.5hr drive or Metro North station near by. Hiking trails, fishing, kayaking many outdoor activities along the Hudson. Woodbury commons outlets 15min away for shopping enthusiasts.
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Popular amenities for Highland Falls holiday rentals
Other great holiday rentals in Highland Falls
Highland Falls Home away from Home. Walk to Thayer
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Quiet, Cozy, Private Suite ~1/2 mile to West Point
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Rockbound Escape
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Old Grad House, within Cadet Walking Privileges
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Delightful Home!
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West Point Apartment/Highland Falls NY
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West Point Hudson Valley Getaway
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Cornwall on Hudson Private Apartment
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When is the best time to visit Highland Falls?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $467 NZD | $467 NZD | $382 NZD | $434 NZD | $472 NZD | $488 NZD | $442 NZD | $449 NZD | $444 NZD | $484 NZD | $521 NZD | $458 NZD |
| 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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