Oakland Vacations from $291

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

Your Oakland Vacation

Say bye-bye to planning hassles and hello to a Oakland vacation package. With everything organized before you leave, you can focus on discovering this city, starting with Soulard, which is great for distilleries and craft breweries, bars and pubs and markets. Ready to venture out and explore? Grants Farm, Magic House - St. Louis Childrens Museum and Saint Louis Galleria Mall are just three of the top places to visit during your trip to Oakland. Your dream Oakland vacation is a couple of clicks away. Browse flights, accommodations and more on Expedia for a getaway that's tailored to suit your style.

The Latest Oakland vacation packages

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $536, price is now $291 per person
$291
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,677 reviews)
My husband and I stayed here on our wedding night. We parked in the parking garage after checking in and were able to go right into the hallway near the elevators. The jacuzzi tub was amazing! I loved that they had towels specifically for makeup as well as a makeup wipe by the sink in the bathroom because I had forgotten to bring my own. The bed was so comfortable and you couldn’t hear other people in the hallway. The continental breakfast served what most hotels serve but everything tasted so much better! We are planning on staying again on our first anniversary!

Reviewed on Nov 6, 2026

Remodeled and Inviting Free EV

Remodeled and Inviting Free EV

2 out of 5
Price was $660, price is now $422 per person
$422
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.4/10 Exceptional! (3 reviews)
We had a great time with my family ❤️ thank you

Reviewed on Oct 12, 2026

The Cheshire

The Cheshire

4 out of 5
Price was $547, price is now $414 per person
$414
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,010 reviews)

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was $417, price is now $321 per person
$321
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.4/10 Exceptional! (708 reviews)

Don't see what you're looking for?
See all available trips from Columbus to Oakland
View all trips

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

The Gateway Arch National Park & Museum

StL's Signature "Sights and Bites" - Private Tour in St. Louis

$175
per adult
StL's Signature "Sights and Bites" - Private Tour in St. Louis
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

$24
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
Self-Guided Audio Tour of Gateway Arch National Park & St. Louis

Self-Guided Audio Tour of Gateway Arch National Park & St. Louis

$15
per traveler
Self-Guided Audio Tour of Gateway Arch National Park & St. Louis
See all activities in Oakland

Oakland Hotel Deals

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
$90 nightly
The price is $107 total per night from Nov 11 to Nov 12
$107 total
Nov 11 - Nov 12
Total with taxes and fees
Pear Tree Inn St. Louis Airport
Drury Plaza Hotel St. Louis at the Arch

Drury Plaza Hotel St. Louis at the Arch

3 out of 5
2 South 4th Street St. Louis MO
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $168 total per night from Nov 11 to Nov 12
$168 total
Nov 11 - Nov 12
Total with taxes and fees
Drury Plaza Hotel St. Louis at the Arch
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
$113 nightly
The price is $133 total per night from Nov 27 to Nov 28
$133 total
Nov 27 - Nov 28
Total with taxes and fees
Hyatt Regency St. Louis at The Arch
See all 1,928 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.

Find the Best Oakland Vacation Packages

Oakland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lambert-St. Louis Intl. Airport (STL)
Population
1,400
Top Sights
St. Louis Zoo, Fox Theater and Magic House - St. Louis Childrens Museum

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Oakland vacation package cost?
Offering great value package deals from $291 on Expedia, you'll be thrilled with how little a vacation to Oakland costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Oakland?
You're likely to find lower rates and better availability in January, October and December. Check out our cheap Oakland vacation packages and you could get some great off-season deals.
How many days is enough for Oakland?
The ideal length of your Oakland vacation depends on what you'd like to see. Usually, a handful of days to a week will give you enough time to go to all the major attractions 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 vacation as a package?
Expedia vacation 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 vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Oakland?
If you've got your Oakland vacation 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.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
If you're anything like us, you love going away but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Oakland trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.