Town of Highlands vacation rentals

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May 2025

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Discover a selection of 17 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.

Vacation rentals with weekly discounts - Town of Highlands

Showing deals for:Aug 1 - Aug 8

Exceptional

(5 reviews)

Majestic RiverView Estate - Breathtaking Views

Beacon, NY

10% off

Luxurious & Historic Orchard Hill Estate farmhouse/mansion built 1859

Exceptional

(77 reviews)

Stunning Mansion, Pool, Pets, Hot Tub, Fire Pit, Hike, Secluded luxury, 1 hr NYC

Harriman, NY

10% off

Warm and cozy queen sized bedroom, sound proof walls and dim lighting.

Exceptional

(14 reviews)

LOCATION LOCATION LOCATION IN THE HEART OF BEACON & RIGHT ON MAIN STREET.

Beacon, NY

20% off

The front door leads to a porch, patio, and small yard.

Wonderful

(25 reviews)

Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.

Cortlandt, NY

5% off

Exceptional

(109 reviews)

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery, NY

12% off

Exceptional

(19 reviews)

Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

Beacon, NY

10% off

Find spaces that suit your style

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Condo/Apartment

Find the best place to stay - Town of Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Sleeps 4 · 1 bedroom · 1 bathroom

Charming and private 3-bedroom home – minutes from West Point and Bear Mountain!

Sleeps 7 · 3 bedrooms · 2 bathrooms

Top rated rentals - Town of Highlands

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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)
West Point Golf Course (2.9 mi / 4.6 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)

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?

One of the more popular neighborhoods for a Town of Highlands vacation home is Highland Falls. When you lock in a Vrbo vacation rental, you can look forward to having the entire place to yourself. So you don’t have to share it with anybody except for your favorite people.

What is the most popular type of vacation rental accommodation in Town of Highlands?

The most popular types of vacation rentals in Town of Highlands are apartments. Looking for something different? Vrbo has a variety of options to match the unique needs of our guests, so you’ll see vacation properties in loads of shapes and sizes. The perfect home away from home is waiting for you — get yours today.

How much does it cost to rent a vacation rental in Town of Highlands?

Length of stay, property type and season are some things that can determine the price of a vacation home. Simply click on your travel dates to find your perfect fit. From comfy cottages to expansive villas, all Vrbo vacation rentals offer incredible value.

How much does it cost to rent a beach house in Town of Highlands?

Prices for beach houses in Town of Highlands differ depending on the size and style of the property and time of year you’re traveling. Just enter your travel dates into Vrbo and the number of guests to see your rental options and prices. From there you can use our filter tool to narrow your search by nearby activities, ratings, amenities and more.

Are there pet-friendly vacation rentals in Town of Highlands?

With 14 vacation rentals that host pets, your happy hound can join you on your Town of Highlands getaway. Use the filter tool to search our pet-friendly vacation rentals and find the pawfect pad on Vrbo.

Can I rent a house with a pool in Town of Highlands?

Mark the “pool” box in our handy filter tool and select from two houses with private pools in Town of Highlands on Vrbo. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your vacation home has its own swimming pool.

What are popular rental amenities in Town of Highlands?

A swimming pool, a garden and a fireplace head the list of most popular rental amenities in Town of Highlands. Whether you’re taking a trip on your own, with your other half or a group of best friends, Vrbo can help you find a vacation rental that matches your tastes with all the options you need.

Are there large group vacation rentals in Town of Highlands?

Yes, you’ll find eight vacation homes in Town of Highlands that can sleep five or more guests. From family reunions to special occasions, these stays have ample space to chill out with your favorite people.

Are there vacation rentals in Town of Highlands that welcome kids?

Town of Highlands has 14 family-friendly vacation rentals to choose from. And finding a stay that welcomes children is super easy with Vrbo’s “Properties good for families” filter. On top of having the entire place to yourselves, you can also look forward to perks and amenities like multiple bedrooms, kitchens and pools.

What are the top attractions for families in Town of Highlands?

Keep the kids happy at these top family-friendly attractions in Town of Highlands:

West Point Museum
Michie Stadium
West Point Golf Course

Are there one-bedroom vacation rentals in Town of Highlands?

You’ll find five one-bedroom properties in Town of Highlands to select from. A one-bedroom vacation rental is a wonderful choice if it’s only you and your partner or if you’re traveling alone. Add in more space, privacy and convenience than a regular hotel, and you’re bound to have an unforgettable break.

Can I find two-bedroom vacation rentals in Town of Highlands?

Gather your nearest and dearest and experience complete comfort and privacy in one of the two two-bedroom vacation properties Town of Highlands has to offer.

Are there vacation rentals with WiFi in Town of Highlands?

Pick from six vacation rentals with WiFi in Town of Highlands. If you’d like to disconnect from the world on your trip, but still need to be connected to the web, these properties have just 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?

Pick your dates and then use the filter tool to see vacation rentals with air conditioning in Town of Highlands on Vrbo. With 14 air-conditioned properties to choose from here, you can enjoy a comfortable and cool stay.

How old do you have to be to rent a vacation rental in Town of Highlands?

We recommend checking with the Town of Highlands vacation home you’d like on Vrbo as the minimum age varies. However, typically it’s 16, 18 or 21.

How long can I rent a vacation rental in Town of Highlands for?

It’s really down to the Town of Highlands property. To browse available options offering extended stays, just type your dates and number of guests into the Vrbo search page. You can enjoy having the entire place to yourself, as well as amenities such as a fully-equipped kitchen, air conditioning and a backyard where the kids can play. Keep an eye out for any long-term stays that offer weekly or monthly discounts.

Does Vrbo offer discounts for vacation homes in Town of Highlands?

Weekend break or extended escape, Vrbo has some fantastic deals and discounts in Town of Highlands to suit your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or check out what’s recently been added with one of our newly listed homes. Whatever you’re after, you’ll find the perfect place to stay — without spending a fortune.