Highland Holidays

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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
Craftsman styled home in the heart of downtown Highland

Craftsman styled home in the heart of downtown Highland

Highland
9.8/10 Exceptional! (60 reviews)
"This house is in a great location with lots of space for a large group of people. We rented this for my son’s wedding weekend hosting several family members staying with us. Everyone loved their space and the overall home. Lots of parking. Very close to the Old Wick Factory, same owners. Very nice ..."

Reviewed on 14 Aug 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
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.

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.