A building with a clock tower, a sign reading "City Hall," and American flags.

Highland Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Highland vacation rentals

Living area

Guest suite in belleville

Guest suite in belleville
Belleville
10.0 out of 10, Exceptional, (1 review)
"I really enjoyed staying at Sara's property. It was comfortable with lots of comfortable couches and a nice view out the windows. The bedroom had blackout curtains and was really quiet for a good sleep. The kitchen facilities were good for a nice coffee in the morning and microwaving a quick dinner. I appreciated the nightlights and other small touches. The shower was great. All in all, I really enjoyed my stay!"
United States
Darci T.
$171 nightly
The price is $181
Jul 3 - Jul 4
Total with taxes and fees
Guest suite in belleville
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in gorgeous Glen Carbon with AC

Spacious 5-bedroom house in gorgeous Glen Carbon with AC
Glen Carbon
8.4 out of 10, Very Good, (7 reviews)
"Great place to stay "
United States
Karl W.
$439 nightly
The price is $465
Jun 29 - Jun 30
Total with taxes and fees
Spacious 5-bedroom house in gorgeous Glen Carbon with AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Highland Hotel Reviews

Super 8 by Wyndham Troy IL/St. Louis Area

Super 8 by Wyndham Troy IL/St. Louis Area

8/10 Good
"No thanks"
Candice 1-night trip
Posted 3 hours ago
Super 8 by Wyndham Troy IL/St. Louis Area

Find out more about Highland

Everything you need to know about Highland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $181 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Highland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Highland?

Yes, we have vacation rentals near the most popular points of interest in Highland, or you can go with a secluded option if you want a relaxing place to stay. Our travelers say Highland has a good selection of restaurants. Make sure you have time to check out the architecture and lake views during your trip.

What's the top vacation rental that Highland has to offer?

Craftsman styled home in the heart of downtown Highland: This Highland vacation home rental is located in the city center and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Highland?

Expedia has 3 vacation rentals for your stay in Highland.

What can I see and do in Highland?

While you're exploring the area, Silver Lake Park and O'Fallon Family Sports Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Korte Recreation Center and Copper Dock Winery.

What are vacation rentals like in Highland?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Highland. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family getaway.