Oakland Vacations from $358

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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
HoteLumiere at the Arch - A Caesars Rewards Destination
The Cheshire
Home2 Suites by Hilton St. Louis/Forest Park
Marriott St. Louis West
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Oakland Hotel Deals

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

4 out of 5
421 N 8th St St. Louis MO
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $128 total per night from Nov 30 to Dec 1
$128 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (1,124 reviews)
Hotel is great we will definitely stay here again. But we don’t usually eat breakfast.

Reviewed on Nov 24, 2025

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel
Forest Park Hotel by MDR

Forest Park Hotel by MDR

3 out of 5
5915 Wilson Ave St. Louis MO
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Nov 27 to Nov 28
$109 total
Nov 27 - Nov 28
Total with taxes and fees
7.4/10 Good! (1,242 reviews)
Great location

Reviewed on Nov 22, 2025

Forest Park Hotel by MDR
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
$95 nightly
The price is $111 total per night from Nov 28 to Nov 29
$111 total
Nov 28 - Nov 29
Total with taxes and fees
8.4/10 Very Good! (4,006 reviews)
Taylor, at the front desk, was amazing and so helpful. She answered my questions with ease during check-in, and continued to help throughout my stay. Taylor deserves a huge Thank you!

Reviewed on Nov 22, 2025

Hyatt Regency St. Louis at The Arch
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

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Frequently asked questions

How much does an Oakland vacation package cost?
Offering great value package deals from $358 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.