Overland Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best Overland Vacation Packages
Overland Hotel Deals
Hyatt Regency St. Louis at The Arch
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
₩185,275
₩218,493 total
Sep 6 - Sep 7
includes taxes & fees
Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
₩128,959
₩150,544 total
Sep 6 - Sep 7
includes taxes & fees
9/10 Wonderful! (3,338 reviews)
"Original reservation not honored Room was not clean Room was musty. Filters for ac units were dirty Water spots in ceiling Peeling paint Unable to use fan because it only had one speed-high. Breakfast was awesome"
Reviewed on Aug 26, 2026
Hollywood Casino & Hotel St. Louis
777 Casino Center Drive Maryland Heights MO
Fully refundableReserve now, pay when you stay
₩126,686
₩188,881 total
Aug 27 - Aug 28
includes taxes & fees
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 Overland attractions
St. Louis Car Museum
9.2/10 (5 reviews)
You can spend time exploring the galleries in St. Louis Car Museum during your travels in Overland. Experience the great live music and acclaimed theater scene in this family-friendly area.
Frequently asked questions
How much does an Overland vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Overland costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Overland?
You can typically find reduced prices and better availability in January, April and December. Explore our cheap Overland vacation packages and you could land some great off-season deals.
How many days is enough for Overland?
With a well-planned schedule, you can easily tick off the most popular Overland sights in a handful of days. But if you want to discover hidden gems or go on day trips, consider booking your Overland vacation for longer.
How to find the best Overland package deals?
Use Expedia's handy filters to help you find some fabulous Overland package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Overland package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book an Overland vacation as a package?
You can enjoy significant savings on your Overland escape by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Overland?
If you're considering a spur-of-the-moment Overland adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Overland?
- Choose when to travel: Check your schedule and get packing. Your preferred time of year and the available activities will also help you decide when to vacation in Overland.
- Calculate your budget: Ensure you have enough money to pay for everything from meals and transportation to flights and activities. Your hotel will likely be the biggest expense during your trip to Overland.
- Decide your trip length: Consider how long you want to spend exploring Overland. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your accommodations and airfare: After you've settled on your dates and duration, book the right Overland 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.
