Highland Vacations from $256

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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.
Crowne Plaza St. Louis Airport by IHG

Crowne Plaza St. Louis Airport by IHG

3.5 out of 5
Price was $352, price is now $256 per person
$256
per person
Dec 15 - Dec 18
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8/10 Very Good! (1,005 reviews)
Perfect hotel for my three day trip! Nice breakfast buffet, gym and overall ambience. Rooms could use some updating as they have not been remodeled in several years. I would definitely stay again.

Reviewed on Sep 27, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $601, price is now $329 per person
$329
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,581 reviews)
Visited to do some writing. Staff was friendly and helpful, all amenities were clean and functional. Wildwood area is pretty quiet after 8.

Reviewed on Oct 5, 2025

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Price was $428, price is now $294 per person
$294
per person
Dec 15 - Dec 18
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,005 reviews)
Why would you charge 25& for parking!? Why would that not be included in the fee for hotel. Rediculous

Reviewed on Oct 6, 2025

The Cheshire

The Cheshire

4 out of 5
Price was $413, price is now $299 per person
$299
per person
Dec 15 - Dec 18
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.6/10 Excellent! (1,003 reviews)
Cute place. A/c in room could have worked better

Reviewed on Oct 5, 2025

Hampton Inn By Hilton St Louis Airport

Hampton Inn By Hilton St Louis Airport

2.5 out of 5
Woodson Terrace
Price was $422, price is now $308 per person
$308
per person
Dec 15 - Dec 18
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (62 reviews)
All areas was kept clean and breakfast options was great

Reviewed on Oct 4, 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
8/10 Very Good! (622 reviews)
"Parking was well lit and convenient. Room was clean, ac could have worked better. Tv had no guide or anything in the room to tell you what the channels were."

Reviewed on Oct 5, 2025

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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! (63 reviews)
"The host was very helpful with trying to accommodate an additional night, but in the end our flight limited our stay to the original dates. All 3 floors of the house were clean, orderly, and cleverly renovated to maximize space for groups. But floors could also be compartmentalized with separate ..."

Reviewed on Sep 30, 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! (2 reviews)
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 113 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.

Highland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
MidAmerica-St. Louis Airport (BLV)
Population
9,800
Max Temp Winter
40ºF
Max Temp Summer
80ºF
Top Sights
Copper Dock Winery, Silver Lake Park and McKendree University

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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 $256 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.