Highland Vacation Packages

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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.

Top Highland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was CA $1,284, price is now CA $1,000 per person
CA $1,000
per person
Dec 18 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
9.2/10 Wonderful! (1,677 reviews)
Everything was good. Seemed that the property was not full but we were forced into a suite.

Reviewed on Nov 7, 2026

The Cheshire

The Cheshire

4 out of 5
Price was CA $2,103, price is now CA $1,692 per person
CA $1,692
per person
Dec 16 - Dec 23
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,010 reviews)
Room was dirty as well as the property

Reviewed on Nov 7, 2026

Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Price was CA $2,091, price is now CA $1,735 per person
CA $1,735
per person
Dec 16 - Dec 23
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9/10 Wonderful! (2,047 reviews)
Moonrise is a quirky and unique hotel in a great neighborhood. I will gladly stay there again in the future.

Reviewed on Nov 9, 2026

Residence Inn by Marriott St Louis Downtown

Residence Inn by Marriott St Louis Downtown

3 out of 5
Midtown
Price was CA $1,628, price is now CA $1,366 per person
CA $1,366
per person
Dec 16 - Dec 23
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
7.8/10 Good! (1,001 reviews)

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was CA $2,151, price is now CA $1,809 per person
CA $1,809
per person
Dec 16 - Dec 23
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.6/10 Excellent! (1,080 reviews)
We were here for a wedding. Our room was very nice but my son’s bathroom was disgusting and not clean, they had to switch rooms and the only compensation they gave them was a food voucher. Not acceptable with blood and vomit not cleaned from previous guest. We expected more for this caliber of hotel.

Reviewed on Nov 8, 2026

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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 CA $127 per night from Nov 29 to Nov 30
CA $127
CA $141 total
Nov 29 - Nov 30
includes taxes & fees
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! (93 reviews)
"Host provided excellent communication and responsiveness. House with three levels was perfect for our group of families attending awesome event at Olde Wicks Factory venue, so close and accessible. Plenty of parking in close proximity to entries."

Reviewed on Nov 1, 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 Jun 20, 2026

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The Loft on the Square
See all 112 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.
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Stay near popular Highland attractions

Silver Lake Park

8.8/10 (5 reviews)
Explore the great outdoors at Silver Lake Park, a lovely green space in Highland. Stroll along the lakeside or experience the area's festivals.
See properties

Frequently asked questions

How much does a Highland vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,000 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 many days is enough for Highland?
Typically, a handful of days is enough to see the main attractions during your Highland vacation. But if you'd like to have some time to chill out or go on day tours, think about extending your itinerary.
Is it worth booking a vacation package to Highland?
Highland is a good vacation destination with attractions like Silver Lake Park among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Highland vacation promises fun for everyone.
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.