Overland Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Overland Vacation Packages

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 SARĀ 571 per night from Jul 31 to Aug 1
SARĀ 571
SARĀ 674 total
31 Jul - 1 Aug
includes taxes & fees
8.6/10 Excellent! (4,129 reviews)
"Great location!"

Reviewed on 18 July 2026

Hyatt Regency St. Louis at The Arch
Clayton Plaza Hotel & Extended Stay

Clayton Plaza Hotel & Extended Stay

3.5 out of 5
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
The price is SARĀ 363 per night from Aug 9 to Aug 10
SARĀ 363
SARĀ 424 total
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (3,260 reviews)
"N/A"

Reviewed on 18 July 2026

Clayton Plaza Hotel & Extended Stay
Hollywood Casino & Hotel St. Louis

Hollywood Casino & Hotel St. Louis

3.5 out of 5
777 Casino Center Drive Maryland Heights MO
Fully refundableReserve now, pay when you stay
The price is SARĀ 488 per night from Jul 20 to Jul 21
SARĀ 488
SARĀ 624 total
20 Jul - 21 Jul
includes taxes & fees
Hollywood Casino & Hotel St. Louis
See all 2,043 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.

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.
See properties

Frequently asked questions

How much does an Overland vacation package cost?
Offering excellent value package deals 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 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 favorite 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.