Overland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Ready to book your vacation to Overland?
Overland Hotel Deals
Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
CA $127
CA $148 total
Oct 25 - Oct 26
includes taxes & fees
8.8/10 Excellent! (3,474 reviews)
"Hotel staff were excellent, friendly, professional and by far the best reason to re-book. The hotel itself was very clean, located near professional buildings/courts and some eateries within walking distance. The room was clean as well and nicely proportioned with some of the best mattresses/bedding ..."
Reviewed on Oct 13, 2026
Pear Tree Inn St. Louis Airport
10810 Pear Tree Ln St. Ann MO
Fully refundableReserve now, pay when you stay
CA $126
CA $149 total
Oct 27 - Oct 28
includes taxes & fees
9.2/10 Wonderful! (3,290 reviews)
"The property was great but the breakfast menu was the same every morning. I would’ve liked a little more variety. The happy hour cocktails were nice. The room and property were clean. I would’ve liked highly recommend thus property."
Reviewed on Oct 14, 2026
Drury Plaza Hotel St. Louis at the Arch
2 South 4th Street St. Louis MO
Fully refundableReserve now, pay when you stay
CA $192
CA $224 total
Oct 25 - Oct 26
includes taxes & fees
9.6/10 Exceptional! (3,797 reviews)
"I loved the happy hour, you get a voucher for 3 free alcoholic beverages and the food was delicious."
Reviewed on Oct 13, 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.
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 acclaimed theater scene and great live music 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 $245
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 $1,266 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.
