Town of Highlands holiday rentals

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Discover a selection of 16 homes and other holiday rentals in Town of Highlands that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and garden. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
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  • More quality time
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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Book a holiday rental for your Town of Highlands getaway

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

Sightseeing in and around Town of Highlands

Are you looking for attractions to see during your stay? Venture out of your holiday home and check out everything that makes Town of Highlands a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 looking for fun outdoor activities or just want to spend some time taking in the scenery, Town of Highlands is a great place to get outside. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • 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 holiday home?
Among the more popular neighbourhoods for a Town of Highlands holiday home is Highland Falls. When you book a Stayz holiday home, 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 holiday home 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. Stayz has holiday homes 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 holiday home in Town of Highlands?
Season, property type and length of stay are some factors that can influence the price of a holiday home. Simply click on your travel dates to find your ideal match. From cosy cabins to expansive luxury villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Town of Highlands?
The average price for a holiday 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 Stayz 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 holiday homes 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 holiday homes on Stayz. 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 Stayz. Gentle soak, ball games or noodle joust? Free time is up to you when your Stayz holiday property has its own pool.
What are popular home amenities in Town of Highlands?
An electric car charging station, a water view and a swimming pool top the list of most popular home amenities in Town of Highlands. Whether you’re travelling as a party of one, with your other half or as a family group, Stayz will help you find a holiday home that fits your style with all the features you need.
Are there large group holiday homes 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, Stayz will help you book a comfortable space to fit the occasion.
Are there holiday homes in Town of Highlands that welcome kids?
Town of Highlands has 12 family-friendly holiday homes. And securing a stay that welcomes youngsters is a breeze with Stayz’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 holiday homes in Town of Highlands?
Town of Highlands has five one-bedroom homes on offer. Typically situated in sought-after areas because of their smaller size, a one-bedroom holiday property is great if you’re travelling 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 holiday homes in Town of Highlands?
Take off with your loved ones and experience complete comfort and privacy in one of the two two-bedroom holiday homes Town of Highlands has to offer.
Are there holiday homes with WiFi in Town of Highlands?
There are six holiday homes with WiFi in Town of Highlands. If you want to disconnect from the world while on holiday, but still want to be connected to the internet, these getaways have what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Town of Highlands?
Town of Highlands has 12 holiday homes where you can spend your days in air-conditioned comfort. To book a stay on Stayz 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 holiday home in Town of Highlands?
The minimum age requirements can vary across properties on Stayz, so be sure to look at the rules of the holiday home in Town of Highlands you’re interested in. But usually, it’s 16, 18 or 21.
How long can I rent a holiday home in Town of Highlands for?
The amount of time you can book a Town of Highlands holiday home 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 holiday homes might also offer weekly or monthly discounts, so you can stay even longer for less.

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