Highland Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Highland

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
8/10 Very Good! (600 reviews)
"You should sell some type of food or snacks. We came back from a wedding and NOTHING to eat. No where in town open or able to deliver. Breakfast was ok...not good. but better than nothing. I went at 6am, there was sausage but no waffles...lol husband came at 9am....waffles but no sausage. we made ..."

Reviewed on 18 Aug, 2025

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Seasons Inn & Suites Highland
Baymont by Wyndham Highland

Baymont by Wyndham Highland

2 out of 5
20 Central Boulevard, Highland, IL
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Baymont by Wyndham Highland
Drury Inn & Suites St. Louis Fairview Heights

Drury Inn & Suites St. Louis Fairview Heights

3 out of 5
12 Ludwig Dr, Fairview Heights, IL
The price is S$136 per night from 2 Sept to 3 Sept
S$136
2 Sept - 3 Sept
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"The hotel offers a great price - value ratio, esp considering that 2 meals are included. All employees I dealt with were extremely friendly and helpful. This was my first stay in a Drury Hotel but I will definitively stay in more."

Reviewed on 24 Aug, 2025

Drury Inn & Suites St. Louis Fairview Heights
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.

Frequently asked questions

How much does a Highland holiday package cost?
You can grab a holiday package to this popular destination on Expedia. But how much your holiday to Highland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Highland?
You're likely to find lower prices and better availability in January, February and September. Browse our cheap Highland holiday packages and you could score some great off-season deals.
How many days is enough for Highland?
The ideal duration for your Highland holiday depends on what you'd like to see and do. Generally, a few days to a week will give you time to visit all the major sights and discover some hidden treasures along the way.
Is it worth booking a holiday package to Highland?
It's no wonder a Highland holiday is on the to-do list of many travellers. Leading attractions like Silver Lake Park are just the start 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 holiday package as early as possible.
Is it cheaper to book a Highland holiday as a package?
Expedia holiday 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 holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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.
How to plan a trip to Highland?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Highland.
  2. Set a budget: Consider expenses such as food, flights and transportation when working out how much to save for your trip to Highland. Then, select a property that works with your budget, whether that's an affordable stay or a deluxe getaway.
  3. Decide how long to go for: Now that you know more about Highland, you can figure out the right length of your break. Pull together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Highland holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.