Highland Vacations from $275

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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
Price was $569, price is now $275 per person
$275
per person
Dec 18 - Dec 21
found 2 hours ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
9.2/10 Wonderful! (1,677 reviews)

Remodeled and Inviting Free EV

Remodeled and Inviting Free EV

2 out of 5
Save 100% on your flight
Price was $1,399, price is now $813 per person
$813
per person
Jan 18 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.4/10 Exceptional! (3 reviews)
We had a great time with my family ❤️ thank you

Reviewed on Oct 12, 2026

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Save 100% on your flight
Price was $1,207, price is now $855 per person
$855
per person
Jan 18 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.6/10 Excellent! (1,080 reviews)
I was kind of worried staying here, especially with the deal that was going on but truly no regrets. Upon check in, they had multiple staff members available which is uncommon these days and they were nice. We booked a regular king suite and it was huge and spotless! They have an indoor/outdoor pool and jacuzzi available, they were huge. We did stay during the week so the restaurants were not operating at they do on the weekends but they still have a little “deli” available all night with some quick decent options or you can always doordash. They serve coffee/breakfast as well. I did not know until we went to the casino that people could smoke. The upper level of the casino is non smoking but there was no bar up there, not really any people either so we decided to just be mindful of where we sat down stairs. Bar is reasonably priced as well. The only thing that I found annoying was that the machines would be dirty as in cigarette ashes and ashtrays so I would have to move along to find something clean. They have vending available by the check in desk and in the same hallway as the casino. Definitely would return.

Reviewed on Oct 28, 2026

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $1,116, price is now $829 per person
$829
per person
Jan 18 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.8/10 Excellent! (1,010 reviews)

Crowne Plaza St. Louis Airport by IHG

Crowne Plaza St. Louis Airport by IHG

3.5 out of 5
Price was $844, price is now $646 per person
$646
per person
Jan 18 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8/10 Very Good! (1,001 reviews)

Don't see what you're looking for?
See all available trips from Columbus to Highland
View all trips

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.
See properties

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
$102 nightly
The price is $113 total per night from Nov 25 to Nov 26
$113 total
Nov 25 - Nov 26
Total with taxes and fees
8/10 Very Good! (698 reviews)
"Good luck"

Reviewed on Oct 25, 2026

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! (91 reviews)
"Very nice. Very clean. Enjoyed our stay and would definitely go back. Thanks"

Reviewed on Oct 12, 2026

Get rates
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

Get rates
The Loft on the Square
See all 110 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

What's the best vacation package for Highland?
For travelers seeking romantic getaways in Highland, a package built around a stay at Seasons Inn & Suites Highland offers a comfortable base. This hotel, located about 1 mile from central Highland, features an indoor pool and free WiFi, with travelers often praising the nice staff and comfortable rooms, noting the beautiful location. It's also a convenient starting point for exploring scenic outdoor areas like Silver Lake Park, about 1 mile away.

Families planning a Highland vacation package will find Seasons Inn & Suites Highland a practical choice. Its indoor pool provides a great option for kids, and the complimentary breakfast helps start the day easily. The hotel is also well-situated for family-friendly attractions such as Korte Recreation Center, about 2 miles from central Highland.

If you're looking for the best value vacation packages in Highland, Seasons Inn & Suites Highland is a strong option, as nearly all hotels in the area fall into a midrange price tier. Its free breakfast and free WiFi add to the overall value, making it a budget-friendly choice for your trip.
How can I save money on a Highland vacation package?
When you bundle, you can save up to 30%*. To save money on a Highland package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Highland?
Highland is an outdoor and nature destination, offering a variety of activities for your Highland vacation:

Browse and book things to do in Highland on Expedia.
Do you need to rent a car in Highland, or is public transport enough?
For a Highland vacation package, a rental car is highly recommended to explore the area. Highland is an outdoor and nature destination, and its attractions are spread across the area, making a rental car the most flexible option for your Highland vacation packages with flights. For instance, popular spots like Copper Dock Winery are about 14 miles from central Highland, and Cave of The Mounds National Natural Landmark is about 16 miles away. St. Louis Lambert International Airport (STL) is about 37 miles from central Highland, and a car allows you to easily reach these natural sites and other points of interest at your own pace.
Can I change or cancel my Highland vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Highland vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Highland vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Highland vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Highland?
To find last-minute vacation packages to Highland, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Highland vacation packages?
Free cancellation on a Highland vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Highland vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Highland getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Highland vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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.