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.
Moonrise Hotel
Delmar Loop
Price was CA $1,112, price is now CA $950 per person
CA $950
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
9/10 Wonderful! (1,981 reviews)
Front desk staff were so very welcoming and helpful. They started our stay off well after a long day of travel. The room was clean and comfortable.
Reviewed on Jun 23, 2026
The Wildwood Hotel
Price was CA $1,462, price is now CA $1,061 per person
CA $1,061
per person
Aug 6 - Aug 9
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
9.2/10 Wonderful! (1,667 reviews)
I absolutely love the wildwood. Best place to stay near St Louis. I will be staying with them again.
Reviewed on Jun 21, 2026
Residence Inn by Marriott St Louis Downtown
Midtown
Price was CA $1,611, price is now CA $1,239 per person
CA $1,239
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
7.8/10 Good! (1,002 reviews)
Suite was well stocked with utensils etc. The room was clean. Staff was nice. Pool was small and our bathroom door in our room didn’t latch, which was tough with 2 toddlers waddling about.
Reviewed on May 20, 2026
Highland Hotel Deals
Seasons Inn & Suites Highland
20 Central Blvd Highland IL
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Jun 25 to Jun 26
CA $149
CA $166 total
Jun 25 - Jun 26
includes taxes & fees
8/10 Very good! (663 reviews)
"The desk staff were not very courteous and very unprofessional. The breakfast was not very good. The person at the desk was not helpful when asking questions about extra napkins and we were told the refrigerator was broken. The creamer for the coffee which needed refrigeration was left out at all ..."
Reviewed on Jun 15, 2026
Craftsman styled home in the heart of downtown Highland
Highland IL
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
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
