Photo by Joe Farmer

Highland vacation rentals

We found 140 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of vacation rentals in Highland that are perfect for your trip. Vacation homes provide the amenities you need and want for you and your friends, family, or even pets, like WiFi and parking. At the end of the day, you'll be able to choose a rental for everyone's needs, including accessible or non-smoking choices.

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

The charming city of Highland awaits you

Enjoy the churches and other features of Highland. Travelers to this romantic city praise the ice skating, basketball games and bird watching. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Highland

Do you want to find attractions to see in the area? Venture out of your vacation home and experience everything that makes Highland a fun spot to vacation. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Albanese Candy Factory (11 mi / 17.8 km)
  • Deep River Water Park (13 mi / 21 km)
  • Turkey Creek Golf Course (6.5 mi / 10.4 km)
  • Lost Marsh Golf Course (7.9 mi / 12.7 km)
  • Ravisloe Country Club (11.3 mi / 18.1 km)
  • Harborside International Golf Center (12.2 mi / 19.6 km)

Exploring the natural landscape of Highland

Whether you're looking for adventure or just want to spend some time taking in the scenery, Highland is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Indiana Dunes National Park (21.2 mi / 34.1 km)
  • Centennial Park (3.1 mi / 5 km)
  • Hammond Sportsplex & Community Center (3.1 mi / 5.1 km)
  • Whihala Beach (10.2 mi / 16.4 km)
  • Lake Street Beach (10.5 mi / 16.9 km)
  • Crown Point Sports Complex (10.9 mi / 17.5 km)

Transportation to and around Highland

The nearest airport is in Chicago Midway Airport (MDW), located 22 mi (35.5 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Chicago O'Hare Intl. Airport (ORD), which is 37.4 mi (60.2 km) away.

Frequently asked questions

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

According to our research, houses are the most in-demand type of vacation property in Highland. But as you'd expect, everyone's idea of an awesome stay will differ. Vrbo has vacation rentals of all shapes and sizes, and we'll help you find the perfect match.

How much does it cost to rent a vacation rental in Highland?

Length of stay, property type and time of year are some of the conditions that can influence the price of a vacation home. Simply add your travel dates to find the ultimate escape. From comfy cabins to sprawling villas, all Vrbo vacation rentals provide incredible value.

How much does it cost to rent a beach house in Highland?

The average price for a vacation home close to the beach in Highland depends on when you're visiting the area and the size and style of property you're searching for. You can quickly and easily find prices on Vrbo by entering the dates you'll be traveling. Then make use of the filter tool to select the number of bedrooms and amenities that you require, like a pool, WiFi and air conditioning.

Are there pet-friendly vacation rentals in Highland?

With three properties that host four-legged guests, your furry friend can join in the fun on your Highland getaway. Use the filter tool to browse our pet-friendly vacation rentals and find a vacation home that'll set tails wagging on Vrbo.

What are popular rental amenities in Highland?

A garden, off-street parking options and an oven top the list of most popular rental amenities in Highland. Whether you're planning to travel alone, with your sweetheart or a bunch of friends, Vrbo will help you find a vacation home that fits your style with all the extras you're looking for.

Are there vacation rentals in Highland that welcome kids?

Highland has three family-friendly vacation rentals to choose from. And securing a stay that welcomes little ones is simple with our "Properties good for families" filter. In addition to having the whole place to yourselves, you'll get perks and conveniences such as extra bedrooms, private pools and yards.

What are the top attractions for families in Highland?

Keep the kids happy at these fantastic family-friendly attractions in Highland:

  • Mascot Hall Of Fame
  • Hammond Sportsplex & Community Center
  • Midwest Training & Ice Center

Can I find two-bedroom vacation rentals in Highland?

Pick from two two-bedroom vacation homes in Highland. Settle the kids into the second room or fill it with a couple of your besties. There's a spot for whoever's fortunate enough to be coming along for the ride.

How can I find vacation rentals with air conditioning in Highland?

You can choose from three Vrbo vacation homes with air conditioning in Highland providing that cool, cool breeze and extra element of comfort. Simply enter your preferred travel dates and then make use of our filter tool to help you find stays with air conditioning.

How old do you have to be to rent a vacation rental in Highland?

The minimum required age is typically 16, 18 or 21. It can differ from one property to another on Vrbo, so check the rules of your preferred Highland vacation home before booking your stay.

How long can I rent a vacation rental in Highland for?

The amount of time you can stay in a Highland vacation home for depends on the property. Just tap in your preferred travel dates to view options that offer extended stays. They have all you require to make your extended break more enjoyable such as air conditioning and laundries. Some properties may also offer weekly or monthly discounts, so you can stick around for longer for less.