Overland Vacation Packages
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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!
Top Overland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
CA $837
per person
Oct 22 - Oct 25
found 22 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
9.2/10 Wonderful! (1,665 reviews)
The location is ideal because it’s in the heart of Wildwood. Quaint and safe. The rate is also great.
I will say that the exterior is beautiful but the interior could really use an upgrade. The furniture and decor is outdated.
The bed was a bit firm for me but it was comfortable enough.
Clean and safe. Dogs allowed. And the movie theater is across the street. It’s walking distance to Walgreen’s and Starbucks and Dierberg’s grocery store.
It’s honestly more affordable than the chains and just as good.
Reviewed on Aug 26, 2026
Remodeled and Inviting Free EV
CA $1,560
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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
Ready to book your vacation to Overland?
Overland Hotel Deals
Hyatt Regency St. Louis at The Arch
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
CA $186
CA $219 total
Aug 28 - Aug 29
includes taxes & fees
Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
CA $125
CA $146 total
Sep 6 - Sep 7
includes taxes & fees
9/10 Wonderful! (3,336 reviews)
"I’d stay again"
Reviewed on Aug 26, 2026
Hollywood Casino & Hotel St. Louis
777 Casino Center Drive Maryland Heights MO
Fully refundableReserve now, pay when you stay
CA $127
CA $189 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.
What to do in Overland
St. Louis Ghost Tour: Sinister Sins & Shadows
CA $34
per adult
100% of travellers recommend
StL's Signature "Sights and Bites" - Private Tour in St. Louis
CA $246
per adult
Lemp Haunted Neighborhood Walking Tour
CA $35
per adult
84% of travellers recommend
Frequently asked questions
How much does an Overland vacation package cost?
Offering excellent value package deals from CA $837 on Expedia, you'll be pleasantly surprised at how much a vacation to Overland costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Overland?
January, April and December are the best times to search for cheap Overland vacation packages. Opting to travel in quieter periods means you can typically find lower prices on flights and hotels.
How many days is enough for Overland?
Allow at least 2 days for your Overland vacation to enjoy everything that makes this place unique. Stroll around key neighbourhoods, including Downtown Clayton and Richmond Heights. Then check out major sights like St. Louis Art Museum and The Loop. With a well-organized itinerary, you'll be kept busy with room for some me-time too. Want to travel outside of Overland? Consider an excursion or two.
How to find the best Overland package deals?
Landing a cheap Overland package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most wallet-friendly Overland package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book an Overland vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and hotels separately. Better still, you can customize your Overland escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Overland?
Secure incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Overland adventure.
How to plan a trip to Overland?
- Choose your travel dates: The things you plan to do in Overland and your favourite season will help you decide when to travel.
- Work out your budget: Ensure you have enough money to cover everything from meals and transportation to experiences and flights. Your hotel will likely be the biggest expense during your trip to Overland.
- Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to experience in Overland. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find an Overland vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
