Town of Highlands vacation rentals

We found 291 vacation rentals — enter your dates for availability

Discover a selection of 16 homes and other vacation rentals in Town of Highlands that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll have the amenities you expect and more, such as WiFi and cable TV. Whatever you're looking for, you'll be able to choose a rental for everyone's 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 Town of Highlands getaway

Learn about the unique charm of Town of Highlands with a stay in a private vacation home. This city has something for everyone. Woodbury Common Premium Outlets and LEGOLAND® New York are just a couple of the must-sees in the area. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Sightseeing in and around Town of Highlands

Are you hoping to find things to do during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Town of Highlands has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • LEGOLAND® New York (17.6 mi / 28.4 km)
  • Brotherhood Winery (11.3 mi / 18.2 km)
  • Putnam County Golf Course (11.5 mi / 18.5 km)
  • Ice Time Sports Complex (13.8 mi / 22.3 km)
  • SplashDown Beach (14.2 mi / 22.8 km)
  • New York Country Club (14.8 mi / 23.9 km)

Exploring the natural features in Town of Highlands

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Town of Highlands is a great place to get out in nature. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Storm King State Park (5.2 mi / 8.4 km)
  • Hudson Highlands State Park (6.5 mi / 10.4 km)
  • Storm King Art Center (6.8 mi / 11 km)
  • Oscawana Lake (7.2 mi / 11.5 km)
  • Lake Tiorati Beach (7.8 mi / 12.5 km)
  • Lake Welch Beach (9.4 mi / 15.1 km)

Frequently asked questions

What is the best area to stay in Town of Highlands when booking a vacation rental?
Among the more popular neighborhoods for a Town of Highlands vacation home is Highland Falls. When you book a Vrbo vacation rental, you can look forward to having the whole place to yourself. That means you don’t have to share it with anybody except for your people.
What is the most popular type of vacation rental accommodation in Town of Highlands?
Based on our research, houses are the most desirable type of property in Town of Highlands. But that goes without saying, everyone’s idea of an awesome stay can differ. Vrbo has vacation rentals in a variety of shapes and sizes, and we’ll help you discover the perfect fit for you.
How much does it cost to rent a vacation rental in Town of Highlands?
Season, property type and length of stay are some factors that can influence the price of a vacation home. Simply click on your travel dates to find your ideal match. From cozy cabins to expansive luxury villas, all Vrbo vacation rentals offer unbeatable value.
How much does it cost to rent a beach house in Town of Highlands?
The average price for a vacation home by the beach in Town of Highlands will depend on when you’ll be there and the style and size of property you want. Find prices easily on Vrbo by entering your preferred travel dates. Then use our handy filter tool to choose the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a pool.
Are there pet-friendly vacation rentals in Town of Highlands?
Pack a travel bag and a bone for the pup in your life because Town of Highlands has 12 stays that put out the welcome mat to pets. Let your furriest pal enjoy fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Town of Highlands?
Tick the “pool” box in our filter tool and you can choose from two houses with private pools in Town of Highlands on Vrbo. Gentle soak, ball games or noodle joust? Free time is up to you when your Vrbo vacation property has its own pool.
What are popular rental amenities in Town of Highlands?
An electric car charging station, a water view and a swimming pool top the list of most popular rental amenities in Town of Highlands. Whether you’re traveling as a party of one, with your other half or as a family group, Vrbo will help you find a vacation rental that fits your style with all the features you need.
Are there large group vacation rentals in Town of Highlands?
With eight Town of Highlands properties that can sleep five or more people, you can bring a few extra buddies or family members along. Whether you’re planning a casual get-together or a special celebration, Vrbo will help you book a comfortable space to fit the occasion.
Are there vacation rentals in Town of Highlands that welcome kids?
Town of Highlands has 12 family-friendly vacation homes. And securing a stay that welcomes youngsters is a breeze with Vrbo’s “Properties good for families” filter. Besides having the entire place to yourselves, you’ll get access to amenities and perks like extra bedrooms, kitchens and private pools.
What are the top attractions for families in Town of Highlands?
Keep the kids occupied at these popular family-friendly attractions in Town of Highlands:

  • Peekskill Museum
  • Hudson Highlands Nature Museum
  • Lincoln Depot Museum

Are there one-bedroom vacation rentals in Town of Highlands?
Town of Highlands has five one-bedroom rentals on offer. Typically situated in sought-after areas because of their smaller size, a one-bedroom vacation property is great if you’re traveling with a buddy or your partner. And with comforts such as full kitchens and more privacy than a standard hotel, you’ll be able to chill out while exploring this top destination.
Can I find two-bedroom vacation rentals in Town of Highlands?
Take off with your loved ones and experience complete comfort and privacy in one of the two two-bedroom vacation rentals Town of Highlands has to offer.
Are there vacation rentals with WiFi in Town of Highlands?
There are six vacation rentals with WiFi in Town of Highlands. If you want to disconnect from the world while on vacation, but still want to be connected to the internet, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Town of Highlands?
Town of Highlands has 12 vacation rentals where you can spend your days in air-conditioned comfort. To book a stay on Vrbo that comes with this perk, choose your travel dates and use the filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Town of Highlands?
The minimum age requirements can vary across properties on Vrbo, so be sure to look at the rules of the vacation rental in Town of Highlands you’re interested in. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Town of Highlands for?
The amount of time you can book a Town of Highlands vacation rental for is up to each property. Just put in your dates of travel to see options offering longer term stays. They have all the things you need to make your extended getaway more convenient and enjoyable, like kitchens and laundries. Some vacation homes might also offer weekly or monthly discounts, so you can stay even longer for less.

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