Oakland Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Oakland
Hyatt Regency St. Louis at The Arch
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
S$202
28 Aug - 29 Aug
includes taxes & fees
8.6/10 Excellent! (4,181 reviews)
"This is THE hotel to stay at if you're visiting the Arch. It's a VERY short walk--cross street and you're at the park entrance in front of the arch. We got an arch view room and it did not disappoint. Only negative is long waits for the elevators at peak times and there's no chairs to sit in while ..."
Reviewed on 16 Aug, 2026
Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
S$137
30 Aug - 31 Aug
includes taxes & fees
8.8/10 Excellent! (3,330 reviews)
"Pool area not available."
Reviewed on 16 Aug, 2026
Hollywood Casino & Hotel St. Louis
777 Casino Center Drive Maryland Heights MO
Fully refundableReserve now, pay when you stay
S$187
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (2,222 reviews)
"Smell of fish in the hall outside room. Otherwise great."
Reviewed on 15 Aug, 2026
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 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.
What to do in Oakland
StL's Signature "Sights and Bites" - Private Tour in St. Louis
S$226
per adult
Downtown St. Louis Smartphone Guided Audio Walking Tour App
S$10
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
S$31
per adult
100% of travellers recommend
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?
- 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.
- 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.
- 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.
- 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
