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
- Holiday Inn St. Louis Arpt West-Earth City by IHG
Dec 18 - Dec 20Holiday Inn St. Louis Arpt West-Earth City by IHG + Flight
Earth City2 nights3.5 star property7.6/10 - Good (1,000 reviews)"It was clean and have no complaints."Reviewed November 3, 2026Roundtrip • Calgary (YYC) - St. Louis (STL)YYC - STL • 1 stop STL - YYC • 1 stopCA $970CA $911found 11 hours agoper traveller - The Wildwood Hotel
Dec 18 - Dec 20The Wildwood Hotel + Flight
Wildwood2 nights3.5 star property9.2/10 - Wonderful (1,682 reviews)"Everything was good. Seemed that the property was not full but we were forced into a suite."Reviewed November 7, 2026Roundtrip • Calgary (YYC) - St. Louis (STL)YYC - STL • 1 stop STL - YYC • 1 stopCA $1,284CA $1,000found 11 hours agoper traveller - Hampton Inn St. Charles St. Peters
Dec 18 - Dec 20Hampton Inn St. Charles St. Peters + Flight
St. Charles2 nights2.5 star property8.2/10 - Very good (1,001 reviews)Roundtrip • Calgary (YYC) - St. Louis (STL)YYC - STL • 1 stop STL - YYC • 1 stopCA $992CA $954found 11 hours agoper traveller - Hyatt Place St. Louis/Chesterfield
Dec 18 - Dec 20Hyatt Place St. Louis/Chesterfield + Flight
Chesterfield2 nights3.0 star property9.6/10 - Exceptional (1,011 reviews)Roundtrip • Calgary (YYC) - St. Louis (STL)YYC - STL • 1 stop STL - YYC • 1 stopCA $1,034CA $997found 11 hours agoper traveller - Courtyard St. Louis Airport/Earth City
Dec 18 - Dec 20Courtyard St. Louis Airport/Earth City + Flight
Bridgeton2 nights3.0 star property8.4/10 - Very good (1,001 reviews)Roundtrip • Calgary (YYC) - St. Louis (STL)YYC - STL • 1 stop STL - YYC • 1 stopCA $1,033CA $998found 11 hours agoper traveller
Where to stay in Overland
Breckenridge Hills
Sycamore Hills
Overland Hotel Deals
Wingate by Wyndham St. Louis Airport
Wingate by Wyndham St. Louis Airport
Drury Inn & Suites St. Louis Airport
Drury Inn & Suites St. Louis Airport
Renaissance St. Louis Airport Hotel
Renaissance St. Louis Airport Hotel
Hampton Inn By Hilton St Louis Airport
Hampton Inn By Hilton St Louis Airport
Best Western Plus St. Louis West-Westport
Best Western Plus St. Louis West-Westport"Location was convenient to major highways. Room was large and clean. Breakfast was more than continental which was nice. Staff was friendly and helpful. Hallways didn't smell the best but overall the hotel was perfect for a place to sleep."
Frequently Asked Questions
How much does an Overland vacation package cost?
Offering excellent value package deals from CA $911 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.