Highland Vacations from $250

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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.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $438, price is now $250 per person
$250
per person
Apr 12 - Apr 15
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
Everything was great

Reviewed on Feb 23, 2026

Landing Apartments - Eureka

Landing Apartments - Eureka

4 out of 5
Save 100% on your flight
Price was $785, price is now $595 per person
$595
per person
Apr 12 - Apr 15
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
No reviews
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Price was $350, price is now $267 per person
$267
per person
Apr 12 - Apr 15
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (779 reviews)
Everything was 5 star

Reviewed on Feb 13, 2026

Hilton Pennywell St. Louis at the Arch

Hilton Pennywell St. Louis at the Arch

4 out of 5
Downtown St. Louis
Save 100% on your flight
Price was $569, price is now $439 per person
$439
per person
Apr 12 - Apr 15
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (996 reviews)
Yea but truly my wife was the star of theshow

Reviewed on Feb 23, 2026

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was $625, price is now $494 per person
$494
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to St. Louis (STL)
9.4/10 Exceptional! (425 reviews)
Very clean rooms. Clean and fresh feeling. Appreciated the bathrooms looking so nice and clean too! Will definitely stay there again. Only thing I’d change is I wish there were microwaves in the room.

Reviewed on Feb 16, 2026

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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
$118 nightly
The price is $131 total per night from Mar 2 to Mar 3
$131 total
Mar 2 - Mar 3
Total with taxes and fees
8/10 Very Good! (630 reviews)
No one mentioned that TV cable was out before check in. No discount was given.

Reviewed on Feb 7, 2026

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

Craftsman styled home in the heart of downtown Highland

Highland IL
10/10 Exceptional! (71 reviews)
Our location and space in the house.

Reviewed on Jan 15, 2026

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

The Loft on the Square

Highland IL
10/10 Exceptional! (6 reviews)
Our 2nd stay at this property, and our experience was amazing once again. The host decorated for the holidays, and it made our stay even more special. All of the added touches are so well done. We will be back!

Reviewed on Dec 28, 2025

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The Loft on the Square
See all 114 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.

Find the Best Highland Vacation Packages

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 $250 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

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