Overland Vacations from $373
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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.
The Cheshire
$531
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,005 reviews)
We loved our stay at the Cheshire. The author themed rooms were a hit with this bookish couple. Great location with easy access to the highway, Forest Park, and more. And the Fox and the Hound is a great little cozy space!
Reviewed on Aug 31, 2026
Remodeled and Inviting Free EV
$524
per person
Oct 22 - Oct 25
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9/10 Wonderful! (2 reviews)
It was nice to stay for a weekend but the neighborhood was nice I like the location where it wasn't too far from grocery stores food areas the only thing I was saying is it's nothing for the kids to do but overall I like it
Reviewed on Aug 7, 2026
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.
What to do in Overland
St. Louis Ghost Tour: Sinister Sins & Shadows
$24
per adult
100% of travellers recommend
StL's Signature "Sights and Bites" - Private Tour in St. Louis
$175
per adult
Lemp Haunted Neighborhood Walking Tour
$25
per adult
84% of travellers recommend
Overland Hotel Deals
Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
$97 nightly
$113 total
Sep 6 - Sep 7
Total with taxes and fees
9/10 Wonderful! (3,366 reviews)
"Multiple stays in the past"
Reviewed on Aug 31, 2026
Hyatt Regency St. Louis at The Arch
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
$134 nightly
$158 total
Sep 4 - Sep 5
Total with taxes and fees
8.6/10 Excellent! (4,219 reviews)
"Husband and I stayed for 2 nights for a baseball game. The check in staff was so helpful and sweet. Everyone was very nice from check in to valet. The restaurants were very good and not crazy over priced. The property is in walking distance to everything. We had a great view of the city. Our bed ..."
Reviewed on Aug 31, 2026
Hollywood Casino & Hotel St. Louis
777 Casino Center Drive Maryland Heights MO
Fully refundableReserve now, pay when you stay
$125 nightly
$146 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (2,213 reviews)
"The room was great. Only downside was the tv in the living room didn't work properly but that's not enough for me to take a star away. The room was clean, staff was very helpful and friendly. You have to use a key card to even work the elevator so you don't have to worry about some random person ..."
Reviewed on Aug 31, 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.
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 $373 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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- Old Post Office
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- The MOTO Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
