Highland Vacations from $358

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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 $662, price is now $358 per person
$358
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,668 reviews)
Everything was great. Staff was very helpful and friendly. I will definitely stay here next time I am in Missouri.

Reviewed on Aug 1, 2026

Remodeled and Inviting Free EV

Remodeled and Inviting Free EV

2 out of 5
Save 100% on your flight
Price was $741, price is now $442 per person
$442
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
10/10 Exceptional! (1 review)
The property was excellent, and the home was very warm and welcoming.

Reviewed on Jun 25, 2026

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $616, price is now $394 per person
$394
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,005 reviews)
Very charming property. We loved learning about a new author and the nice breakfast. Free street parking on the street is plentiful so I wouldn't pay for hotel parking. On-site restaurant was very loud and didn't have kid's menu but we made do.

Reviewed on Aug 1, 2026

Residence Inn by Marriott St. Louis West County

Residence Inn by Marriott St. Louis West County

3 out of 5
Save 100% on your flight
Price was $915, price is now $590 per person
$590
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (261 reviews)

Residence Inn by Marriott St Louis Downtown

Residence Inn by Marriott St Louis Downtown

3 out of 5
Midtown
Save 100% on your flight
Price was $579, price is now $376 per person
$376
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
7.8/10 Good! (1,000 reviews)
Check in tooks hours and went beyond 4pm making ua late for tickets we had, room smelled of old cigarettes, getting help with parking tickets was impossible and overall just a disappointment for a Marriott location.

Reviewed on Jul 31, 2026

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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.
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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
$94 nightly
The price is $104 total per night from Aug 2 to Aug 3
$104 total
Aug 2 - Aug 3
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! (82 reviews)
"Checking in and checking out was made simple by the host. It was a great spot for my family to stay during my wedding weekend. During a busy weekend, the location of the house and the host helped everything run smoothly."

Reviewed on Jul 29, 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! (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

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The Loft on the Square
See all 119 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 $358 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.