Highland Vacations from $220

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Your Highland Vacation

When a getaway to the city is calling your name, answer it with a vacation package to Highland. With all your travel arrangements under control before you go, all you need to do here is focus on making unforgettable memories. Korte Recreation Center and Silver Lake Park are among the top attractions to tour during your trip to Highland. Whoever you're going away with and whatever the size of your budget, your dream Highland vacation is only clicks away with Expedia.

The Latest Highland vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
per person
Oct 2 - Oct 4
found 21 hours ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
8.2/10 Very Good! (756 reviews)
I booked online and paid via the app. When I arrived on site they explained they had overbooked and had no rooms available. The staff was amazing and went above and beyond and secured a room at another location. Thank you to the staff for taking care of us.

Reviewed on Jul 26, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9/10 Wonderful! (1,549 reviews)
For the price, this hotel was great. A cheap clean stopover in St. Louis. We were very happy to have cafes and restaurants within walking distance too! And parking was free.

Reviewed on Jul 30, 2025

The Principal Hotel

The Principal Hotel

3.5 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 22
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.8/10 Exceptional! (88 reviews)
Very clean quiet , room excellent ,mattress very comfortable, extra towels Overall experience awesome.

Reviewed on Jul 26, 2025

Hilton Garden Inn St. Louis/O'Fallon MO

Hilton Garden Inn St. Louis/O'Fallon MO

3 out of 5
Save 100% on your flight
per person
Oct 2 - Oct 5
found 21 hours ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
8.8/10 Excellent! (688 reviews)
The food in the restaurant was terrable. I had the meat balls and I could not eat them

Reviewed on Jun 30, 2025

Ballpark Apartments by Barsala

Ballpark Apartments by Barsala

4 out of 5
Downtown St. Louis
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
7.4/10 Good! (9 reviews)
It's a great location, right across from the Ballpark. It is a fairly spartan apartment set-up, with concrete floors.. a little surprising? Parking is on the street or in a pay lot.

Reviewed on Jun 8, 2025

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Discover the most popular places to visit in Highland

Korte Recreation Center

Catch an event at Korte Recreation Center during your trip to Highland. Stroll along the lakeside or experience the area's festivals.

Korte Recreation Center

Highland Hotel Deals

Seasons Inn & Suites Highland

Seasons Inn & Suites Highland

2.5 out of 5
20 Central Blvd, Highland, IL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Aug 11 to Aug 12
$109 total
Aug 11 - Aug 12
Total includes taxes and fees
8/10 Very Good! (592 reviews)
"It was amazing and friendly staff"

Reviewed on Jul 18, 2025

Seasons Inn & Suites Highland
Craftsman styled home in the heart of downtown Highland

Craftsman styled home in the heart of downtown Highland

Highland
9.8/10 Exceptional! (59 reviews)
Wedding 6/28
"Great"

Reviewed on Jul 22, 2025

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Craftsman styled home in the heart of downtown Highland
The Loft on the Square

The Loft on the Square

Highland
10/10 Exceptional! (1 review)
Great local spot
"Everything was clean and exactly like in the photos! She even left us fresh chocolate chip cookies! They had all the essentials (soaps, coffee, paper products, and even a few snack items and cold waters in the refrigerator!) We will definitely stay again!"

Reviewed on Jul 5, 2025

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The Loft on the Square
See all 101 properties in Highland
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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Frequently asked questions

How much does a Highland vacation package cost?
You can grab a vacation package to this popular destination from $220 on Expedia. But how much your vacation to Highland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Highland?
If you're looking to book a cheap Highland vacation package, consider planning a trip in June, September and October. You're likely to find better rates on flights and hotels during these months — ideal for budget-conscious travelers.
How many days is enough for Highland?
With a well-planned schedule, you can easily hit the top Highland sights in a handful of days. But if you'd like to venture off the beaten track or go on day tours, consider booking your Highland vacation for longer.
Is it worth booking a vacation package to Highland?
It's no wonder a Highland vacation is on the must-do list of many travelers. Top attractions like Silver Lake Park are just the beginning of what you can explore here.
How to find the best Highland package deals?
Use Expedia's handy filters to find some tempting Highland package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Highland package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Highland vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Highland vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Highland?
If you have your Highland travel dates finalized, book as early as you can to snap up some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for setting off on a whim.
Does Expedia offer Book Now, Pay Later Highland vacation packages?
Secure your dream escape to Highland with help from our Book Now, Pay Later vacations. No need to scrimp and save or hold off until payday — we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.