Highland Vacations from $399
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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
$399
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,679 reviews)
Room was clean, yet picures and description are a bit deceiving.
Overall, stay was good and would come back again.
Reviewed on Oct 4, 2026
Residence Inn St Louis Westport
Westport
$407
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (429 reviews)
It’s nice place to stay the staff was amazing, the only thing that wasn’t ok to our house keeping enter our room with out permission and we were out and about……
Reviewed on Sep 22, 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
Oct 11 - Oct 12
Total with taxes and fees
8/10 Very Good! (689 reviews)
"Ok"
Reviewed on Sep 29, 2026
Craftsman styled home in the heart of downtown Highland
Highland IL
10/10 Exceptional! (89 reviews)
"Perfect home for a large group!! Plenty of beds ( some of beds had curtains instead of doors, which was fine for us) loved the extra kitchens and bathrooms on each floor. There are lots of steps to most of the bedrooms . There is one bedroom and bathroom on main floor if you have an elderly person ..."
Reviewed on Oct 3, 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 |
More vacations you might like
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
- Bedandbreakfast in Lebanon
- Motels in Highland
- Hilton Hotels in Highland
- 4 Star Hotels in Highland
- Cottages in Pocahontas
- Hotels in Highland
- Pool in Highland
- 3 Star Hotels in Grantfork
- Cabins in Carlyle
- Hotels in Troy
- Hotels in St. Jacob
- Extended Stay America Hotels in Highland
- Hotels in Breese
- Aparthotels in Highland
- Hotels in Lebanon
- Hotels in Pocahontas
- Pet Friendly in Highland
- Flights to O'Fallon
- Flights from Denver (DEN) to Mascoutah (BLV)
- Flights to Breese
- Flights to MidAmerica-St. Louis
- Oceanic Airlines Swanton (TOL) to Mascoutah (BLV) flights
- Flights to Scott Air Force Base
- Flights to Pocahontas
- Flights from Dallas (DFW) to Mascoutah (BLV)
- Oceanic Airlines Indianapolis (IND) to Mascoutah (BLV) flights
- Flights to Highland
- Southwest Illinois All Inclusive Vacation Packages
- Robert Wadlow Statue
- Where to stay in Belleville
- Southwest Illinois All Inclusive Vacation Packages
- Southwest Illinois All Inclusive Vacation Packages
- Where to stay in Southwest Illinois
- Alton Vacations
- Southwest Illinois All Inclusive Vacation Packages
- Southwest Illinois All Inclusive Vacation Packages
- Where to stay in Granite City
- Visit Mascoutah
- Where to stay in Vandalia
- North Metro East All Inclusive Vacation Packages
- Where to stay in O'Fallon
- Visit Alton
- Southwest Illinois All Inclusive Vacation Packages
- Southwest Illinois All Inclusive Vacation Packages
- Where to stay in Grafton
- Visit Okawville
- Salem Vacations
- North Metro East All Inclusive Vacation Packages
- Lebanon Vacations
- North Metro East All Inclusive Vacation Packages
- World's Largest Catsup Bottle
- Korte Recreation Center
- Visit Nashville
- Southwest Illinois All Inclusive Vacation Packages
- Where to stay in Caseyville
- Visit Highland
- Visit East St. Louis
- Where to stay in Edwardsville
- East St. Louis Vacations
- Visit Belleville
- Where to stay in Pontoon Beach
- Belleville Vacations
- Where to stay in Mount Vernon
- Where to stay in Fairview Heights
- Marissa Vacations
- Visit Pocahontas
- Cahokia Mounds State Historic
- Sorento Vacations
- Visit Collinsville
- Nashville Vacations
- Visit Carlyle
- Visit Southwest Illinois
- Visit Edwardsville
- Cahokia Vacations
- Car rentals in Highland
- Van Car Rentals in MidAmerica-St. Louis
- Minivan Car Rentals in Belleville
- Car rentals in Troy
- Car rentals in Breese
- Car rentals in Lebanon
- Enterprise Rental Cars in Highland
- Budget Rental Cars in MidAmerica-St. Louis
- Sports Car Car Rentals in Belleville
- Car rentals in O'Fallon
- Car rental Airport (BLV)
- Hertz Rental Cars in Highland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
