Oakland Holidays

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Your Oakland Holiday

When a city break is calling, answer it with an Oakland holiday package. The neighbourhood of Soulard, which is great for distilleries and craft breweries, bars and pubs and markets, makes a wonderful base for your adventures. Every trip to Oakland needs a well-planned itinerary. Fill yours with big-name attractions like Grants Farm, Magic House - St. Louis Childrens Museum and Saint Louis Galleria Mall. Don't delay your visit to this destination any longer. Your ultimate Oakland holiday is a few clicks away with Expedia.

Oakland Holiday

Oakland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lambert-St. Louis Intl. Airport (STL)
Population
1,400
Max Temp Winter
4ºC
Max Temp Summer
29ºC
Top Sights
St. Louis Zoo, Fox Theatre and Magic House - St. Louis Childrens Museum

Our pick of the best Oakland 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 AU$257 per night from 31 July to 1 Aug
AU$257
31 July - 1 Aug
includes taxes & fees
8.6/10 Excellent! (4,145 reviews)
"Pros: The staff was helpful and kind, location is perfect if planning to attend a St. Louis Cardinals ballgame, there is a Starbucks in building and room was clean. The size of the Junior King Suite is perfect for a family. Cons: The elevators were extremely slow and could not accommodate the large ..."

Reviewed on 26 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 AU$162 per night from 9 Aug to 10 Aug
AU$162
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (3,289 reviews)
"We were not able to check in for 1 1/2 hours past check in due to staff shortage…which is really unacceptable, with only an offer of a bottle of water as you wait. It also made us cut our anniversary time away short as we were rushed to get to the scheduled game. Don’t sell rooms if you don’t have ..."

Reviewed on 26 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 AU$238 per night from 2 Aug to 3 Aug
AU$238
2 Aug - 3 Aug
includes taxes & fees
8.6/10 Excellent! (2,212 reviews)
"Haven’t stayed here before and expected a lot more from a casino/hotel. The hotel room has spackle all over the bathroom walls as if it was under construction and there wasn’t a microwave in the room. Also, when gambling most hotel/casinos that we have stayed provide free drinks, but that was not ..."

Reviewed on 26 July 2026

Hollywood Casino & Hotel St. Louis
See all 1,942 properties in Oakland
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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Oakland attractions

Grant's Trail - Backstopper's Park Trailhead

You can take time to visit Grant's Trail - Backstopper's Park Trailhead during your travels to Oakland.
See properties

What to do in Oakland

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

AU$35
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
Landmarks Downtown-West Walking Tour

Landmarks Downtown-West Walking Tour

AU$28
per adult
Landmarks Downtown-West Walking Tour
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

AU$36
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
See all activities in Oakland

Frequently asked questions

How much does an Oakland holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Oakland costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Oakland?
If you'd like to score a cheap Oakland holiday package, consider visiting in January, February and November. You're likely to find lower prices on flights and accommodation during these months — perfect for travellers wishing to save money.
How many days is enough for Oakland?
The ideal duration of your Oakland holiday depends on what you'd like to see. Generally, a handful of days to a week will give you plenty of time to check out all the main sights and discover some hidden gems along the way.
How to find the best Oakland package deals?
Start your search for an Oakland package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Oakland package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oakland escape off to a flying start.
Is it cheaper to book an Oakland holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Oakland holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Oakland?
If you've got your Oakland holiday dates finalized, book as early as you can to grab some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Oakland?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to go to Oakland.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to activities and airfares. Your hotel will probably be the biggest expense during your trip to Oakland.
  3. Determine how many days away: Start by compiling a list of the activities and attractions you want to get to in Oakland. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Oakland holiday package.

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