Overland Vacations from $381

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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.
Elimwood Hotel, a Ramada by Wyndham

Elimwood Hotel, a Ramada by Wyndham

3 out of 5
Riverport
Price was $509, price is now $381 per person
$381
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
7.6/10 Good! (1,009 reviews)

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $1,182, price is now $715 per person
$715
per person
Dec 21 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,677 reviews)

Remodeled and Inviting Free EV

Remodeled and Inviting Free EV

2 out of 5
Price was $646, price is now $420 per person
$420
per person
Feb 2 - Feb 5
found 8 hours ago
Roundtrip flight included
Minneapolis (MSP) to St. Louis (STL)
9.4/10 Exceptional! (3 reviews)
We had a great time with my family ❤️ thank you

Reviewed on Oct 12, 2026

The Cheshire

The Cheshire

4 out of 5
Price was $1,136, price is now $791 per person
$791
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,010 reviews)
I love absolutely the Cheshire but I was a little disappointed at the cleanliness and condition of the property during our last visit. Our rooms floors were dirty, the baseboards were covered in dust, and the furniture in the rooms were pretty dinged up. We also booked a room for four guests and realized we were only left two towels, two wash cloths, and barely enough toiletries to share between us. As someone who is in the hospitality business myself, I expected a little more attention to detail. Especially for what we paid for the one night stay. We love the tavern and the food from there is always a hit after a long day of exploring the city. The breakfast was great, as usual. We will absolutely be back but wanted to be honest about our room

Reviewed on Nov 10, 2026

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was $746, price is now $559 per person
$559
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.4/10 Exceptional! (708 reviews)
Nice hotel. Staff was friendly. Wash U has a beautiful campus. Will stay again!

Reviewed on Nov 9, 2026

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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.
See properties

What to do in Overland

The Gateway Arch National Park & Museum

StL's Signature "Sights and Bites" - Private Tour in St. Louis

$175
per adult
StL's Signature "Sights and Bites" - Private Tour in St. Louis
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

$24
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
St. Louis: Lemp Haunted Neighborhood Ghost Tour

St. Louis: Lemp Haunted Neighborhood Ghost Tour

$27
per adult
St. Louis: Lemp Haunted Neighborhood Ghost Tour
See all activities in Overland

Overland Hotel Deals

Pear Tree Inn St. Louis Airport

Pear Tree Inn St. Louis Airport

2.5 out of 5
10810 Pear Tree Ln St. Ann MO
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $107 total per night from Nov 15 to Nov 16
$107 total
Nov 15 - Nov 16
Total with taxes and fees
9.4/10 Exceptional! (3,358 reviews)
"Nachos and drinks at happy hour. Full hot breakfast. Lovely room"

Reviewed on Nov 11, 2026

Pear Tree Inn St. Louis Airport
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
$144 nightly
The price is $168 total per night from Nov 16 to Nov 17
$168 total
Nov 16 - Nov 17
Total with taxes and fees
Drury Plaza Hotel St. Louis at the Arch
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
$113 nightly
The price is $133 total per night from Nov 27 to Nov 28
$133 total
Nov 27 - Nov 28
Total with taxes and fees
Hyatt Regency St. Louis at The Arch
See all 2,051 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.

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

What is the best time to go to Overland?
The best time to go for an Overland vacation package is from June to July, which are the peak times for visitors. These months offer the highest demand for an Overland vacation, suggesting favorable conditions for exploring the city's family-friendly attractions and outdoor activities.

For travelers seeking a quieter experience, January is typically the lowest month for visitors, with November and February also seeing fewer crowds.
How can I save money on a Overland vacation package?
When you bundle, you can save up to 30%*. To save money on a Overland package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
Is Overland better suited for a beach vacation or a cultural trip?
Overland is a central urban destination known for its family-friendly attractions and city amenities, offering a rich blend of history and urban exploration for an Overland vacation.

Travelers can explore historic sites like the Lackland House, built around 1844, or the Wild Acres Park, a Renaissance Revival home from 1907. The city also provides access to attractions such as the St. Louis Car Museum and the expansive Forest Park, about 10 miles away, which features various cultural institutions.

An Overland vacation package can be customized to explore these historical and urban highlights.
What are the top things to do in Overland?
An Overland vacation offers a variety of attractions, from local parks to major St. Louis landmarks:

Browse and book things to do in Overland on Expedia.
Do you need to rent a car in Overland, or is public transport enough?
For an Overland vacation package, a rental car offers the most flexibility for exploring the city and its surrounding attractions. While some local points of interest are within a few miles, many popular sites like Forest Park (about 10 miles away) or Enterprise Center (about 19 miles away) are more easily reached by car.

Travelers arriving via St. Louis Lambert International Airport (STL) can arrange for a rental car directly from the airport to begin their Overland vacation packages with flights. This provides convenient access to the area's family-friendly attractions and outdoor activities.
Are there vacation package hotels in Overland within walking distance of restaurants and shops?
Overland vacation package hotels can place you within walking distance of restaurants and shops, particularly around commercial areas.

For example, Staybridge Suites St Louis - Westport by IHG (rated 8.5 out of 10) and Fairfield Inn & Suites St Louis Westport (rated 8.5 out of 10) are both about a 5-minute walk from Westport Plaza, which offers various dining and retail options. Residence Inn St Louis Westport, rated 7.7 out of 10, is also conveniently located about a 5-minute walk from Westport Plaza.

Actual walking routes may differ from straight-line distances, so it's always a good idea to check the map for your selected hotel.
Can I change or cancel my Overland vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Overland vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Overland vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Overland vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Overland?
To find last-minute vacation packages to Overland, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Overland vacation packages?
Free cancellation on a Overland vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Overland vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Overland getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Overland vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.