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Highland Falls vacation rentals

We found 382 vacation rentals — enter your dates for availability

Discover a selection of 14 homes and other vacation rentals in Highland Falls that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation homes have the amenities you expect for your stay, which might include WiFi and a pool. No matter what you're looking for, you'll be sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Book a vacation rental for your Highland Falls getaway

Enjoy the churches and other features of Highland Falls. Renowned for its university setting, shopping and waterfalls, this city welcomes all visitors. Woodbury Common Premium Outlets and LEGOLAND® New York are just a couple of the must-sees in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Highland Falls

Do you want to find attractions to see in the city? Venture out of your cozy vacation rental and experience everything that makes Highland Falls a one-of-a-kind vacation spot. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • LEGOLAND® New York (18 mi / 28.9 km)
  • Putnam County Golf Course (10.8 mi / 17.4 km)
  • Brotherhood Winery (11.1 mi / 17.8 km)
  • SplashDown Beach (12.7 mi / 20.5 km)
  • Ice Time Sports Complex (12.9 mi / 20.7 km)
  • Benmarl Vineyards and Winery (15.5 mi / 24.9 km)

Exploring the natural landscape of Highland Falls

Whether you're looking for adventure or just want to take in the scenery, Highland Falls is a great place to get outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Storm King State Park (4 mi / 6.4 km)
  • Hudson Highlands State Park (5 mi / 8.1 km)
  • Storm King Art Center (6.2 mi / 9.9 km)
  • Oscawana Lake (6.3 mi / 10.1 km)
  • Lake Tiorati Beach (9.1 mi / 14.6 km)
  • Fishkill Ridge (9.7 mi / 15.7 km)

Transportation options to and around Highland Falls

The nearest airport is in Stewart Intl. Airport (SWF), located 11 mi (17.6 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Westchester County Airport (HPN), which is 24.8 mi (40 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Highland Falls?
The most desirable types of vacation rentals in Highland Falls are houses. Prefer something different? Vrbo offers a variety of options to match the unique needs of our guests, so you’ll see vacation homes in all shapes and sizes. The perfect fit is ready and waiting for you — get yours today.
How much does it cost to rent a vacation rental in Highland Falls?
Length of stay, property type and time of year are some of the conditions that can influence the price of a vacation home. Simply click on your travel dates to find your dream escape. From comfy cottages to plush villas, all Vrbo vacation rentals offer terrific value.
How much does it cost to rent a beach house in Highland Falls?
The average price for a vacation home close to the beach in Highland Falls will depend on when you’ll be there and the type and size of property you’re looking for. Find prices easily on Vrbo by entering your travel dates. Then use our filter tool to choose the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a pool.
Are there pet-friendly vacation rentals in Highland Falls?
You’re in luck. There are. Choose from eight vacation homes that roll out the welcome mat in Highland Falls on Vrbo. Our furry friends need a break too, so simply use our search function for pet-friendly vacation rentals to find a pad where Spot can lap up the good times.
Can I rent a house with a pool in Highland Falls?
Pack your swimsuit and inflatable unicorn, because there are two houses with a private pool in Highland Falls. Base yourself at one of these terrific vacation homes and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find the perfect place for a splashing good time!
What are popular rental amenities in Highland Falls?
When it comes to rental amenities that people prefer in Highland Falls, a water view, mountain views and a barbecue grill are at the top of the list. With Vrbo vacation rentals, you’ll have options to match your taste and style, whether you’re planning to get away with family members, friends or even pets.
Are there large group vacation rentals in Highland Falls?
Take your pick of seven Vrbo vacation properties in Highland Falls that can host a group of five or more people. You’ll get all the privacy and room you need to have fun with your favorite people — and no one else.
Are there vacation rentals in Highland Falls that welcome kids?
With eight family-friendly vacation properties available in Highland Falls, now is the perfect time to introduce the kiddos to the magic of travel. Click on our “Properties good for families” filter to locate stays that come with amenities ideal for families on the move, such as living rooms, backyards, bunk beds and hot tubs.
What are the top attractions for families in Highland Falls?
There are loads of cool things to see and do with the family in Highland Falls, including:

  • West Point Museum
  • Michie Stadium
  • Eisenhower Hall Theater

Are there one-bedroom vacation rentals in Highland Falls?
Highland Falls has two one-bedroom rentals on offer. Often positioned in popular areas due to their compact size, a one-bedroom vacation rental is ideal if you’re getting away with your partner or a buddy. And with comforts such as wireless internet and more privacy than a standard hotel, you’ll be able to kick back and relax while exploring this amazing destination.
Can I find two-bedroom vacation rentals in Highland Falls?
Highland Falls has two two-bedroom vacation properties to choose from. Discover a vacation home with all the space and comfort you want at a price you’ll love on Vrbo.
Are there vacation rentals with WiFi in Highland Falls?
Highland Falls has three vacation rentals with WiFi, so you can stay connected while you’re away. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movies with your family to checking emails, these Vrbo homes make it easy to go online.
How can I find vacation rentals with air conditioning in Highland Falls?
Highland Falls has eight vacation rentals where you’ll be able to relax in air-conditioned comfort. To find a stay on Vrbo featuring this amenity, enter your preferred travel dates and use the convenient filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Highland Falls?
You’ll have to check with the Highland Falls vacation home you want on Vrbo as the age limit varies. However, it’s normally 16, 18 or 21.
How long can I rent a vacation rental in Highland Falls for?
The amount of time you can book a Highland Falls vacation rental for is down to each property. Simply put in your dates of travel to find available options offering longer term stays. They have everything you need to make your extended trip more enjoyable and comfortable, like kitchens and air conditioning. Some vacation rentals may also offer weekly or monthly discounts, so you can stay longer for less money.

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