Overland Vacations from $575

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Your Overland Vacation

When a fun city getaway is calling, answer it with a Overland vacation package. The neighborhood of Soulard, which is great for distilleries and craft breweries, bars and pubs and markets, makes an excellent base for your adventures. Fill your itinerary with tours of St. Louis Zoo, St. Louis Art Museum and Washington University in St. Louis, some of the top attractions you really should see during your trip to Overland. Stop dreaming and start doing. Browse the range of options on Expedia today and finally put your Overland vacation plans into action!

The Latest Overland vacation packages

Price found within the past 48 hours. Click for updated prices.
Osage Village Inn Near Lake Ozarks US 54
The Wildwood Hotel
Lodge Of Four Seasons Golf Resort, Marina & Spa
The Knight Center at Washington University
Hermann Grain Bins BNB
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What to do in Overland

Overland Hotel Deals

Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

4 out of 5
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from May 25 to May 26
$149 total
May 25 - May 26
Total with taxes and fees
8.6/10 Excellent! (4,019 reviews)
Liked that it was in walking distance to the stadium and could leave our car in parking until 4.

Reviewed on Apr 27, 2026

Hyatt Regency St. Louis at The Arch
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

3 out of 5
1088 South Highway Drive Fenton MO
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $103 total per night from May 17 to May 18
$103 total
May 17 - May 18
Total with taxes and fees
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham
Hollywood Casino & Hotel St. Louis

Hollywood Casino & Hotel St. Louis

3.5 out of 5
777 Casino Center Drive Maryland Heights MO
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $143 total per night from Apr 28 to Apr 29
$143 total
Apr 28 - Apr 29
Total with taxes and fees
8.4/10 Very Good! (2,187 reviews)
A little on the higher side for the area and amenities but it is a resort. The place was clean and the staff was very welcoming. Would stay again.

Reviewed on Apr 26, 2026

Hollywood Casino & Hotel St. Louis
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.

Find the Best Overland Vacation Packages

Overland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lambert-St. Louis Intl. Airport (STL)
Population
16,000
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
St. Louis Zoo, Fox Theater and Magic House - St. Louis Childrens Museum

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Frequently asked questions

How much does an Overland vacation package cost?
Offering great value package deals from $575 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?
January, October and December are the best times to look for cheap Overland vacation packages. Opting to travel in quieter months means you can typically find lower prices on flights and accommodations.
How many days is enough for Overland?
Typically, a handful of days is enough to see the main sights during your Overland vacation. However, if you want to have more time to unwind or go on day tours, think about extending your trip.
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.
Does Expedia offer Book Now, Pay Later Overland vacation packages?
If you're like us, you love going away but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Overland vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.

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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.