Highland Vacations from $443
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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 Cheshire
$524
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,014 reviews)
A nice, interesting place, in an excellent location, right off the park. Zoo and art museum an easy stroll. My wife and I used a different St. Louis hotel for our annual trip to see my son and his family, but we tried this hotel on a whim and the Cheshire has become our new favorite.
Reviewed on Aug 31, 2026
Remodeled and Inviting Free EV
$524
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9/10 Wonderful! (2 reviews)
It was nice to stay for a weekend but the neighborhood was nice I like the location where it wasn't too far from grocery stores food areas the only thing I was saying is it's nothing for the kids to do but overall I like it
Reviewed on Aug 7, 2026
Stay near popular Highland attractions
Silver Lake Park
8.8/10 (5 reviews)
Silver Lake Park surrounds a 550-acre lake with scenic hiking trails and abundant wildlife. Enjoy boating, fishing, or playing a round at the 18-hole disc golf course while taking in the tranquil woodland setting.
Korte Recreation Center
6.0/10 (1 review)
This community hub features an indoor pool with a lazy river and water slide, plus a fitness center and gymnasium. Enjoy family-friendly recreation year-round, perfect for escaping Illinois weather while staying active.
Highland Hotel Deals
Seasons Inn & Suites Highland
20 Central Blvd Highland IL
Fully refundableReserve now, pay when you stay
$94 nightly
$104 total
Sep 3 - Sep 4
Total with taxes and fees
Craftsman styled home in the heart of downtown Highland
Highland IL
10/10 Exceptional! (85 reviews)
"The house was the perfect size for 8 of us. We were within walking distance of so many things, too."
Reviewed on Aug 25, 2026
The Loft on the Square
Highland IL
10/10 Exceptional! (9 reviews)
"Host was very responsive. We had an issue when our daughter got sick and the host was very helpful."
Reviewed on Jun 20, 2026
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 $443 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.