Overland Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Overland

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 3.998.709 ₫ per night from 31 Jul to 1 Aug
3.998.709 ₫
4.715.637 ₫ total
31 Jul - 1 Aug
includes taxes & fees
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 2.521.636 ₫ per night from 16 Aug to 17 Aug
2.521.636 ₫
2.943.707 ₫ total
16 Aug - 17 Aug
includes taxes & fees
9/10 Wonderful! (3,263 reviews)
"I really liked this property. It’s pretty nice. The shower was the best part. Absolutely loved it. The bed was comfortable and the hvac worked well. The sink needed to be cleaned better. Someone had trimmed their beard and there was beard clippings all around the sink. The type of finish on the sink ..."

Reviewed on 18 Jul 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 3.417.437 ₫ per night from 20 Jul to 21 Jul
3.417.437 ₫
4.371.046 ₫ total
20 Jul - 21 Jul
includes taxes & fees
8.6/10 Excellent! (2,187 reviews)
"Overall, the state was great. It was in a secure area. I didn’t have to worry about certain situations popping off/starting security did their job perfectly. And the staff were very helpful. And very understanding I will definitely book here again."

Reviewed on 18 Jul 2026

Hollywood Casino & Hotel St. Louis
See all 2,044 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 studying the exhibits at St. Louis Car Museum during your travels in Overland. Experience the great live music and acclaimed theatre scene in this family-friendly area.
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Frequently asked questions

How much does an Overland holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Overland costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Overland?
You can typically find reduced prices and better availability in January, April and December. Explore our cheap Overland holiday packages and you could land some great off-season deals.
How many days is enough for Overland?
With a well-planned schedule, you can easily tick off the most popular Overland sights in a handful of days. But if you want to discover hidden gems or go on day trips, consider booking your Overland holiday for longer.
How to find the best Overland package deals?
Use Expedia's handy filters to help you find some fabulous Overland package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Overland package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book an Overland holiday as a package?
You can enjoy significant savings on your Overland escape by booking a personalised holiday package. Check the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Overland?
If you're considering a spur-of-the-moment Overland adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Overland?

  1. Choose when to travel: Check your schedule and get packing. Your preferred time of year and the available activities will also help you decide when to holiday in Overland.
  2. Calculate your budget: Ensure you have enough money to pay for everything from meals and transportation to flights and activities. Your hotel will likely be the biggest expense during your trip to Overland.
  3. Decide your trip length: Consider how long you want to spend exploring Overland. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your accommodation and airfare: After you've settled on your dates and duration, book the right Overland holiday package for you.

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