Overland Vacations from $286
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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
$392
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to St. Louis (STL)
8.8/10 Excellent! (1,014 reviews)
We love the Cheshire - so much character!! We used to stay here when visiting our son at WashU. We will miss it! Great burgers and craft ale next door at Basso's too - and it has its own English-type pub as well!
Reviewed on Sep 2, 2026
The Royal Sonesta Chase Park Plaza St. Louis
Central West End
$415
per person
Oct 8 - Oct 11
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,025 reviews)
The air conditioning vent in our room blew on my face all night so I was cold then hot and back and forth. The final night I had to sleep with the sheet over my head. Also, the cleaning staff forgot to leave us towels one day.
Reviewed on Sep 3, 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
StL's Signature "Sights and Bites" - Private Tour in St. Louis
$175
per adult
St. Louis Ghost Tour: Sinister Sins & Shadows
$24
per adult
100% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
$25
per adult
84% of travellers recommend
Overland Hotel Deals
Hyatt Regency St. Louis at The Arch
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
$143 nightly
$169 total
Sep 5 - Sep 6
Total with taxes and fees
8.6/10 Excellent! (4,205 reviews)
"Staff, Bell Hops, and Valet parking team were excellent. The coffee in the room leaves a lot to be desired, but Starbucks and the hotel offers a great selection down stairs."
Reviewed on Sep 4, 2026
Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
$92 nightly
$107 total
Oct 4 - Oct 5
Total with taxes and fees
Renaissance St. Louis Airport Hotel
9801 Natural Bridge Road St. Louis MO
Fully refundableReserve now, pay when you stay
$119 nightly
$139 total
Sep 18 - Sep 19
Total with taxes and 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.
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 $286 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.
