Highland Holidays from £808

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Your Highland Holiday

When a getaway to the city is calling your name, answer it with a holiday 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 Centre 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 holiday is only clicks away with Expedia.

Top Highland Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hollywood Casino & Hotel St. Louis

Hollywood Casino & Hotel St. Louis

3.5 out of 5
per person
12 Sept - 17 Sept
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
8.4/10 Very Good! (2,036 reviews)
It was nice and relaxing

Reviewed on 10 Aug 2025

Highland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
MidAmerica-St. Louis Airport (BLV)
Population
9,800
Max Temp Winter
4ºC
Max Temp Summer
27ºC
Top Sights
Copper Dock Winery, Silver Lake Park and McKendree University

Top hotels in Highland

Seasons Inn & Suites Highland

Seasons Inn & Suites Highland

2.5 out of 5
20 Central Blvd, Highland, IL
8/10 Very Good! (596 reviews)
Wonderful stay.
"I had a very very relaxing good night sleep and i cant wait to.come visit again. Thankyou"

Reviewed on 3 Aug 2025

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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! (59 reviews)
Wedding 6/28
"Great"

Reviewed on 22 Jul 2025

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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! (1 review)
Great local spot
"Everything was clean and exactly like in the photos! She even left us fresh chocolate chip cookies! They had all the essentials (soaps, coffee, paper products, and even a few snack items and cold waters in the refrigerator!) We will definitely stay again!"

Reviewed on 5 Jul 2025

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The Loft on the Square
See all 108 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Highland travel package cost?
Custom make your Highland travel package from as little as £808. Pick from any combination of flights, hotels and rental cars to create the escape you've long been dreaming about. Don't forget to add on some activities and experiences!
If I'm not able to travel, can I cancel my Highland travel package?
Plans can change without warning, so yes, you can. You may be able to amend or cancel your Highland travel package at no cost within 24 hours of booking. For bookings older than that, you can still make the necessary changes, but your car rental company, airline or hotel may impose a charge. Want more information? Have a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Highland?
Bundle your flight and hotel bookings, throw in extras such as activities, and save with a Highland travel package. You won't just score impressive discounts on your trip — you'll have lots of choice too. When you book with Expedia, you can select from more than 550 partner airlines and 1,000,000 hotels globally. Your next affordable adventure starts right here, right now!
Does Expedia offer Book Now, Pay Later Highland holidays?
Expedia has joined forces with online lender Klarna to make your next break a bit easier on the wallet. Paying by instalment means you can spread the costs of your next adventure, leaving you with more money to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find something that suits your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds right for you, Klarna can help. Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you want to jump on an amazing deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock in your getaway.

Where should I stay in Highland?
With lots to discover in Highland, it'd be convenient for you to book a room in a hotel near its attractions. Silver Lake Park, Korte Recreation Centre and HSHS St Josephs Hospital are some popular ones to put on your itinerary.
What are the top hotels in Highland?
If this will be your first visit to Highland, secure a room at Hyatt Regency Chicago or The Godfrey Hotel Chicago. Both offer friendly service and are favourites among many savvy travellers.
How far in advance should I book my Highland holiday?
While prices change frequently, we generally recommend reserving your seat as early as possible. Most international fares are found on Expedia up to 12 months in advance. If circumstances have left you booking late, you might still get lucky. Low prices to Highland occasionally appear only weeks before departure.
What does an Expedia Highland travel package include?
Flights, hotels and a cool car for all your road trip adventures. Simply choose your preferred bundle and get access to great discounts. Once you've made your booking, add on a few experiences and tours and watch your savings grow. When it comes to planning your Highland getaway, you're the one in control!
What should I know before booking a Highland travel package?
An Expedia travel package can be tailored to your budget and is a great way to make your money go further. What you include is totally up to you. Hotels, rental cars and flights — decide on a combination that works with your plans.
Can I choose my airline with a Highland Expedia travel package?
With a travel package, you're in charge. Whether you want to fly to Highland in business or coach, simply pick from the available airline options. Expedia has access to over 550 airline partners worldwide.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.