Highland Vacations

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Find the Best Highland Vacation Packages

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
The price is AEDĀ 311 per night from Jul 26 to Jul 27
AEDĀ 311
AEDĀ 345 total
26 Jul - 27 Jul
includes taxes & fees
8/10 Very Good! (669 reviews)
"Room was clean and neat. Parking was really easy."

Reviewed on 16 July 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! (81 reviews)
"The house was perfect for the groomsmen to hang out Friday night before the beautiful wedding at the Olde Wicks Factory Venue, and to crash after the celebration Saturday night. Jennifer was great to work with at both the house and at the venue. The location is close to the venue and the boys were ..."

Reviewed on 13 July 2026

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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! (9 reviews)
"Host was very responsive. We had an issue when our daughter got sick and the host was very helpful."

Reviewed on 20 June 2026

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The Loft on the Square
See all 118 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.

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.
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Frequently asked questions

How much does a Highland vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. But how much your vacation to Highland costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Highland?
January, February and September are the best times to search for cheap Highland vacation packages. Choosing to travel in less busy months means you can usually find lower prices on flights and hotels.
How to find the best Highland package deals?
Use Expedia's handy filters to find some unbeatable Highland package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Highland package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Highland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations individually. Better still, you can tailor your Highland trip to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Highland?
If you're considering an impromptu Highland getaway, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Highland?

  1. Choose your dates: What you want to do in Highland and your preferred season will help you decide when to travel.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and activities. Your accommodations will likely be the largest expense during your trip to Highland.
  3. Decide how many days away: Start by making a list of all the activities and sights you'd like to experience in Highland. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your accommodations and airfare: Once you've nailed down your dates and duration, lock in the perfect Highland vacation package for you.