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

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $693, price is now $358 per person
$358
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
18.4/10 Exceptional! (1,600 reviews)
Everything was good except the hot tub was down.

Reviewed on Nov 25, 2025

HoteLumiere at the Arch - A Caesars Rewards Destination

HoteLumiere at the Arch - A Caesars Rewards Destination

4 out of 5
Downtown St. Louis
Save 100% on your flight
Price was $646, price is now $374 per person
$374
per person
Jan 7 - Jan 11
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
13.2/10 Exceptional! (1,001 reviews)
It was very nice resort

Reviewed on Nov 20, 2025

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $649, price is now $418 per person
$418
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
17.2/10 Exceptional! (1,002 reviews)
Great stay! The room could have been a tiny bit cleaner but nothing crazy! Mainly stains on the table and some dusty areas but beds and bathrooms were clean! The staff was super nice and the place was nicely decorated.

Reviewed on Nov 15, 2025

Home2 Suites by Hilton St. Louis/Forest Park

Home2 Suites by Hilton St. Louis/Forest Park

3 out of 5
The Grove
Save 100% on your flight
Price was $737, price is now $483 per person
$483
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
17.2/10 Exceptional! (1,000 reviews)
Everything was perfect A bit more attention to detail is needed. A deep clean on a regular basis.

Reviewed on Nov 10, 2025

Marriott St. Louis West

Marriott St. Louis West

3.5 out of 5
Save 100% on your flight
Price was $574, price is now $377 per person
$377
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
17.2/10 Exceptional! (1,000 reviews)
Parking area felt very safe

Reviewed on Oct 14, 2025

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Discover the most popular places to visit in Oakland

St. Louis Union Station

St. Louis Union Station

4/5(615 reviews)

You can learn about the local history of St. Louis when you make a stop at a well-known site like St. Louis Union Station. Experience the area's great live music or attend a baseball game.

St. Louis Union Station
Gateway Arch showing a city, a skyscraper and skyline

Gateway Arch

4.5/5(2,511 reviews)

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

Gateway Arch
St. Louis Zoo

St. Louis Zoo

4.5/5(1,212 reviews)

In the middle of St. Louis, meet the exotic and endangered animals that live in meticulously recreated ecosystems from all over the world.

St. Louis Zoo

What to do in Oakland

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

$32
per adult
St. Louis Ghost Tour: Sinister Sins & Shadows
St. Louis Arch Walking Tour and Entrance Ticket

St Louis Arch Small Group Walking Tour and Arch Entrance Ticket

$45
per adult
74% of travellers recommend
St Louis Arch Small Group Walking Tour and Arch Entrance Ticket
Step into the shadows and discover the haunting tales of our city's past.

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

$30
per adult
100% of travellers recommend
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
See all activities in Oakland

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
See all 1,744 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

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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.