Highland Vacations from $297

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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 $378, price is now $297 per person
$297
per person
Jul 11 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.4/10 Very Good! (822 reviews)
Great hotel. Clean and the food was good.

Reviewed on May 15, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $707, price is now $497 per person
$497
per person
Aug 4 - Aug 7
found 15 hours ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
9.2/10 Wonderful! (1,649 reviews)
Nice property in the St. Louis area! Very clean and luxurious feel to it. Very safe area as it is up in the mountains and away from the city, police department is even next door. Everything is in walking distance. Our room had a very comfortable king size bed, a couch, nice chair with foot stool, desk with computer chair, fridge and small microwave. The continental breakfast even had Jimmy Dean sausage, egg and cheese biscuits. We were only there one night so we didn't get to enjoy any of the onsite amenities. It is rated as a destination and venue for weddings, etc.

Reviewed on May 17, 2026

Hilton Garden Inn St. Louis/O'Fallon MO

Hilton Garden Inn St. Louis/O'Fallon MO

3 out of 5
Price was $1,004, price is now $767 per person
$767
per person
Jul 12 - Jul 18
found 17 hours ago
Roundtrip non-stop flight included
New York (NYC) to St. Louis (STL)
8.8/10 Excellent! (737 reviews)
Very nice, very clean, comfortable hotel, we’ll definitely be back. We stay in Kansas City quite a bit and have never tried this Hilton before. We found a new favorite.

Reviewed on May 15, 2026

Holiday Inn Express & Suites St. Louis - Chesterfield by IHG

Holiday Inn Express & Suites St. Louis - Chesterfield by IHG

2.5 out of 5
Price was $1,013, price is now $825 per person
$825
per person
Jul 12 - Jul 18
found 17 hours ago
Roundtrip non-stop flight included
New York (NYC) to St. Louis (STL)
9/10 Wonderful! (1,003 reviews)
Outstanding place to stay by far, although the pool is small and could use some attention

Reviewed on May 16, 2026

Hampton Inn St. Charles St. Peters

Hampton Inn St. Charles St. Peters

2.5 out of 5
Price was $882, price is now $722 per person
$722
per person
Jul 12 - Jul 18
found 17 hours ago
Roundtrip non-stop flight included
New York (NYC) to St. Louis (STL)
8/10 Very Good! (1,009 reviews)
Breakfast was good. Room was clean. Staff was friendly and helpful. The ongoing renovation affected experience a little bit.

Reviewed on May 24, 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
$122 nightly
The price is $135 total per night from May 25 to May 26
$135 total
May 25 - May 26
Total with taxes and fees
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! (76 reviews)
"The house was perfect for our large family. We had 14 people and everyone had a comfortable room to sleep in. Jennifer is a super responsive host!"

Reviewed on May 8, 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! (7 reviews)
"Great loft right on the square in Highland!"

Reviewed on Apr 12, 2026

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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 $297 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.