Highland Vacations from $502

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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.
White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
Price was $717, price is now $502 per person
$502
per person
Feb 13 - Feb 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
17.2/10 Exceptional! (123 reviews)
Very clean and very friendly people

Reviewed on Nov 11, 2025

Hilton St. Louis Airport

Hilton St. Louis Airport

3.5 out of 5
Woodson Terrace
Save 100% on your flight
Price was $853, price is now $572 per person
$572
per person
Feb 13 - Feb 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
15.2/10 Exceptional! (1,000 reviews)
The room was clean, the staff was nice, and the hotel had a good atmosphere. The lobby restaurant/bar was busy but not overly crowded. The food was good. The floors with the rooms are quiet.

Reviewed on Nov 15, 2025

Tru By Hilton St. Louis Downtown

Tru By Hilton St. Louis Downtown

2.5 out of 5
Downtown West
Price was $765, price is now $531 per person
$531
per person
Feb 13 - Feb 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
15.2/10 Exceptional! (558 reviews)
I felt that the staff and facility were fine. Location met my needs well. However the phone system was down for the entire time of my stay. There was no communication with the hotel from the room, which may have contributed to my room being opened by staff while I was in the room BOTH DAYS! This was unacceptable.

Reviewed on Nov 18, 2025

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $977, price is now $684 per person
$684
per person
Feb 13 - Feb 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
17.2/10 Exceptional! (1,002 reviews)
Great stay! The room could have been a tiny bit cleaner but nothing crazy! Mainly stains on the table and some dusty areas but beds and bathrooms were clean! The staff was super nice and the place was nicely decorated.

Reviewed on Nov 15, 2025

The West End

The West End

2 out of 5
Central West End
Price was $728, price is now $528 per person
$528
per person
Feb 13 - Feb 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
16.8/10 Exceptional! (389 reviews)
Room was clean, facilities were clean, parking was good. Downsides, needs more furniture in the room. A dresser, and possible a sitting chair. Hot water could be a littlw faster so not so much is wasted.

Reviewed on Nov 22, 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! (627 reviews)
We stayed here at the end of March and the hotel was under complete rehabbing. Bet October not much progress has been made. Room furniture has not been replaced. Heavily worn.

Reviewed on Oct 17, 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 IL
9.8/10 Exceptional! (66 reviews)
Everything was nice

Reviewed on Nov 20, 2025

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Craftsman styled home in the heart of downtown Highland
The Swiss Post Apartment B

The Swiss Post Apartment B

2 out of 5
Highland IL
10/10 Exceptional! (3 reviews)
Tricia was a wonderful host, everything was spotless, well equipped easy and comfortable. A perfect stay.

Reviewed on Nov 12, 2025

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The Swiss Post Apartment B
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 $502 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.

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