Oakland Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

Top hotels in Oakland

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 S$252 per night from 17 Jul to 18 Jul
S$252
17 Jul - 18 Jul
includes taxes & fees
8.6/10 Excellent! (4,157 reviews)
"The shower pressure was lacking but otherwise the property was amazing."

Reviewed on 1 Jul, 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 S$146 per night from 12 Jul to 13 Jul
S$146
12 Jul - 13 Jul
includes taxes & fees
8.8/10 Excellent! (3,249 reviews)
"A very well maintained hotel at a very reasonable price. Excellent location conveniently located for any purpose in Clayton or adjacent University City. Many quality restaurants within short walking distance. The hotel includes a really good full breakfast. Ramp parking is attached. Two big thumbs ..."

Reviewed on 30 Jun, 2026

Clayton Plaza Hotel & Extended Stay
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
The price is S$140 per night from 19 Jul to 20 Jul
S$140
19 Jul - 20 Jul
includes taxes & fees
9.2/10 Wonderful! (3,044 reviews)
"Very good"

Reviewed on 1 Jul, 2026

Pear Tree Inn St. Louis Airport
See all 1,933 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.

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

Best of St. Louis Small Group Tour w/ Arch & River Cruise

St. Louis Premium Small Group Tour With Arch & River Cruise

S$207
per adult
84% of travellers recommend
St. Louis Premium Small Group Tour With Arch & River Cruise
Downtown St. Louis Smartphone Guided Audio Walking Tour App

Downtown St. Louis Smartphone Guided Audio Walking Tour App

S$10
per adult
100% of travellers recommend
Downtown St. Louis Smartphone Guided Audio Walking Tour App
St. Louis Premium Driving Tour with Boat Ride & Arch

St. Louis Premium Driving Tour with Boat Ride & Arch

S$225
per adult
100% of travellers recommend
St. Louis Premium Driving Tour with Boat Ride & Arch
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.

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. 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.