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.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Price was CA $995, price is now CA $776 per person
CA $776
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.2/10 Very Good! (762 reviews)
I booked online and paid via the app. When I arrived on site they explained they had overbooked and had no rooms available. The staff was amazing and went above and beyond and secured a room at another location. Thank you to the staff for taking care of us.

Reviewed on Jul. 26, 2025

DoubleTree by Hilton St. Louis Forest Park

DoubleTree by Hilton St. Louis Forest Park

4 out of 5
Central West End
Price was CA $1,182, price is now CA $922 per person
CA $922
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.2/10 Very Good! (1,000 reviews)
Parking is terrible and you shouldn’t have to pay $15 to park then charge for breakfast when your paying all that money to stay!!

Reviewed on Aug. 23, 2025

White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
Price was CA $1,059, price is now CA $835 per person
CA $835
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.6/10 Excellent! (115 reviews)
It was very clean and nicely decorated. The house is a cool old building. The AC worked great (important, as it was super muggy outside.) I was only there for a couple nights but I think it would have worked well for a longer stay.

Reviewed on Jul. 9, 2025

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was CA $1,213, price is now CA $958 per person
CA $958
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
9.4/10 Exceptional! (376 reviews)
Great location! Very convenient!

Reviewed on Aug. 24, 2025

The Cheshire

The Cheshire

4 out of 5
Price was CA $1,259, price is now CA $1,014 per person
CA $1,014
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.6/10 Excellent! (1,007 reviews)
The Cheshire kept well from of old! We felt back in to the ages yet very 21C amenities. The location is perfect to explore St. Louis. We'd like to come back!

Reviewed on Aug. 23, 2025

Ready to book your vacation to Highland?

 

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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 $138 per night from Aug 26 to Aug 27
CA $138
CA $154 total
Aug 26 - Aug 27
includes taxes & fees
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 Aug. 18, 2025

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! (61 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 Aug. 14, 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 Jul. 5, 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.
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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 from CA $776 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.