Overland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, 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.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was CA $785, price is now CA $595 per person
CA $595
per person
Oct 28 - Oct 30
found 16 hours ago
Roundtrip flight included
Halifax (YHZ) to St. Louis (STL)
9.2/10 Wonderful! (1,558 reviews)
Loved the room, pretty good breakfast in the morning lots of options.

Reviewed on Aug. 20, 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was CA $996, price is now CA $824 per person
CA $824
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.4/10 Very Good! (1,001 reviews)
Loved my stay here will be back

Reviewed on Aug. 13, 2025

CentralWestEnd-WashU-STL- Euphoria

CentralWestEnd-WashU-STL- Euphoria

2 out of 5
Central West End
Price was CA $2,103, price is now CA $1,766 per person
CA $1,766
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
10/10 Exceptional! (1 review)
Spacious 3-Bedroom with King Bed

Spacious 3-Bedroom with King Bed

4 out of 5
Central West End
Price was CA $1,304, price is now CA $1,098 per person
CA $1,098
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9.2/10 Wonderful! (9 reviews)
Overall, we loved the apartment. It was cute, beds were very comfortable.

Reviewed on May 8, 2025

DoubleTree by Hilton St. Louis Forest Park

DoubleTree by Hilton St. Louis Forest Park

4 out of 5
Central West End
Price was CA $847, price is now CA $717 per person
CA $717
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.2/10 Very Good! (1,000 reviews)
Everything is good except the odor in the hall ways

Reviewed on Aug. 17, 2025

Ready to book your vacation to Overland?

 

Choose your dates

Overland Hotel Deals

Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

4 out of 5
315 Chestnut St, St. Louis, MO
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Aug 22 to Aug 23
CA $165
CA $195 total
Aug 22 - Aug 23
includes taxes & fees
8.4/10 Very Good! (3,966 reviews)
When the Yankees are in Town
"Requested early check in by calling direct, I was told not a problem. When we arrived, we were told room was not ready. So we sat 2 hours in the lobby. Shinning movement was young lady who retrieved our vehicle from valet parking Traffic was horrible, and not all elevators working"

Reviewed on Aug. 19, 2025

Hyatt Regency St. Louis at The Arch
Renaissance St. Louis Airport Hotel

Renaissance St. Louis Airport Hotel

4 out of 5
9801 Natural Bridge Road, St. Louis, MO
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Sep 4 to Sep 5
CA $169
CA $198 total
Sep 4 - Sep 5
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"Just ask for early check in. We had to wait 4 hours before we got acroom."

Reviewed on Aug. 18, 2025

Renaissance St. Louis Airport Hotel
Drury Plaza Hotel St. Louis at the Arch

Drury Plaza Hotel St. Louis at the Arch

3 out of 5
2 South 4th Street, St. Louis, MO
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Sep 2 to Sep 3
CA $189
CA $221 total
Sep 2 - Sep 3
includes taxes & fees
9.4/10 Exceptional! (2,973 reviews)
LOVED IT !!!
"Absolutely thrilled with our decision to stay at this hotel. Wonderful staff eager to please. Lots of room in eating area and many staff members to keep things moving. Hotel location is close to centered between Busch Stadium and the Arch. $32 onsite parking is offset with the free evening food and ..."

Reviewed on Aug. 19, 2025

Drury Plaza Hotel St. Louis at the Arch
See all 1,825 properties in Overland
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Overland

Busch Stadium

Busch Stadium

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's great live music or attend a baseball game.

Busch Stadium
Gateway Arch featuring modern architecture, a city and a skyscraper

Gateway Arch

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

Gateway Arch
St. Louis Zoo

St. Louis Zoo

In the middle of St. Louis, meet the exotic and endangered animals that live in meticulously recreated ecosystems from all over the world.

St. Louis Zoo

What to do in Overland

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

CA $31
per adult
96% of travellers recommend
St Louis: City Museum General Admission Ticket
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

CA $44
per adult
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
Best of St. Louis Small Group Tour w/ Arch & River Cruise

Best of St. Louis Small Group Tour w/ Arch & River Cruise

CA $233
per adult
84% of travellers recommend
Best of St. Louis Small Group Tour w/ Arch & River Cruise
See all activities in Overland

Frequently asked questions

How much does an Overland vacation package cost?
Offering excellent value package deals from CA $595 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?

  1. Choose your travel dates: The things you plan to do in Overland and your favourite season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.