Highland Vacations from $460

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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.
Lodge Of Four Seasons Golf Resort, Marina & Spa

Lodge Of Four Seasons Golf Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $674, price is now $460 per person
$460
per person
May 4 - May 11
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
7.4/10 Good! (1,067 reviews)
The staff was pleasant, but she took a long time looking for a junior suite room. Our room was on the first floor without any view. It was terribly outdated and unacceptable. Our second room from the same staff member was a 3rd floor room in better condition but still dated. We had a partial lake view. We were told that only a few of the junior suites have a lake view.

Reviewed on Feb 15, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $1,406, price is now $698 per person
$698
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
Extremely nice hotel with the nicest staff!!

Reviewed on Feb 16, 2026

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Save 100% on your flight
Price was $652, price is now $467 per person
$467
per person
Mar 31 - Apr 4
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.4/10 Exceptional! (425 reviews)
Very clean rooms. Clean and fresh feeling. Appreciated the bathrooms looking so nice and clean too! Will definitely stay there again. Only thing I’d change is I wish there were microwaves in the room.

Reviewed on Feb 16, 2026

Hotel Indigo St Louis - Central West End by IHG

Hotel Indigo St Louis - Central West End by IHG

3.5 out of 5
Central West End
Save 100% on your flight
Price was $987, price is now $709 per person
$709
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (1,000 reviews)
Front Desk was very nice and accommodating. Coffee Shop was wonderful.

Reviewed on Feb 17, 2026

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $1,165, price is now $844 per person
$844
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.6/10 Excellent! (1,002 reviews)
Room was great breakfast was great

Reviewed on Feb 14, 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 $460 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.

Explore a world of travel with Expedia

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