Highland Vacations from $612

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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
Price was $853, price is now $612 per person
$612
per person
Apr 5 - Apr 11
found 1 day ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
8.2/10 Very Good! (779 reviews)
Everything was 5 star

Reviewed on Feb 13, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,272, price is now $727 per person
$727
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
Great staff. Safe place within walking distance of restaurants and activities. Clean room.

Reviewed on Feb 19, 2026

Landing Apartments - Eureka

Landing Apartments - Eureka

4 out of 5
Save 100% on your flight
Price was $1,331, price is now $1,004 per person
$1,004
per person
Apr 8 - Apr 13
found 24 hours ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
No reviews
Spacious 3-Bedroom with King Bed

Spacious 3-Bedroom with King Bed

4 out of 5
Central West End
Save 100% on your flight
Price was $1,270, price is now $977 per person
$977
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
8.6/10 Excellent! (10 reviews)
Clean room nice area

Reviewed on Feb 1, 2026

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 $835, price is now $661 per person
$661
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to St. Louis (STL)
8.8/10 Excellent! (1,022 reviews)
We stayed at the Angad Arts since it was so close to the Fabulous Fox. Very nice hotel with a nice restaurant. Wished weather had been nicer so I could've checked out the rooftop bar. Would definitely stay here again!

Reviewed on Feb 22, 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
$136 nightly
The price is $151 total per night from Feb 26 to Feb 27
$151 total
Feb 26 - Feb 27
Total with taxes and fees
8/10 Very Good! (630 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

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! (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 $612 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.