Oakland Vacations from $177

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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.
21C Museum Hotel St Louis

21C Museum Hotel St Louis

4.5 out of 5
Downtown West
Price was $230, price is now $177 per person
$177
per person
Apr 7 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9/10 Wonderful! (1,633 reviews)
The valet was so nice. She was the best empire

Reviewed on Mar 4, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $663, price is now $445 per person
$445
per person
Apr 10 - Apr 12
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,626 reviews)
2nd time was as good as the first.

Reviewed on Mar 6, 2026

Hotel Saint Louis, Autograph Collection

Hotel Saint Louis, Autograph Collection

4 out of 5
Downtown St. Louis
Save 100% on your flight
Price was $331, price is now $231 per person
$231
per person
Apr 7 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (476 reviews)
Great Luxury Hotel and location.

Reviewed on Mar 4, 2026

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Save 100% on your flight
Price was $252, price is now $180 per person
$180
per person
Apr 7 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,056 reviews)
The property was beautiful and unique. The food was a disappointment. Unfortunately it was just too greasy for us.

Reviewed on Mar 6, 2026

Hampton Inn By Hilton St Louis Airport

Hampton Inn By Hilton St Louis Airport

2.5 out of 5
Woodson Terrace
Price was $282, price is now $220 per person
$220
per person
Apr 7 - Apr 9
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (130 reviews)
The staff does not tell you that they only clean rooms every other day. I had to send for more towels and tissue. Otherwise the stay was fine. Also there is no laundry.

Reviewed on Feb 24, 2026

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Discover the most popular places to visit in Oakland

Union Station, St. Louis, MO

St. Louis Union Station

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
St. Louis Cardinals Baseball.

Busch Stadium

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's fascinating museums or attend a baseball game.

Busch Stadium
Gateway Arch showing a city, a skyscraper and skyline

Gateway Arch

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

Gateway Arch

What to do in Oakland

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

$24
per adult
St. Louis Ghost Tour: Sinister Sins & Shadows
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

$30
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
St. Louis Premium Driving Tour with Boat Ride & Arch

St. Louis Premium Driving Tour with Boat Ride & Arch

$174
per adult
100% of travellers recommend
St. Louis Premium Driving Tour with Boat Ride & Arch
See all activities in Oakland

Oakland Hotel Deals

Pear Tree Inn St. Louis Near Union Station

Pear Tree Inn St. Louis Near Union Station

3 out of 5
2211 Market Street St. Louis MO
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $124 total per night from Mar 15 to Mar 16
$124 total
Mar 15 - Mar 16
Total with taxes and fees
8.8/10 Excellent! (1,868 reviews)
This was a great value hotel. The rooms were clean the air conditioning worked well, and the room included a free three drink happy hour

Reviewed on Mar 7, 2026

Pear Tree Inn St. Louis Near Union Station
21C Museum Hotel St Louis

21C Museum Hotel St Louis

4.5 out of 5
1528 Locust street St. Louis MO
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $138 total per night from Apr 6 to Apr 7
$138 total
Apr 6 - Apr 7
Total with taxes and fees
9/10 Wonderful! (1,639 reviews)
The valet was so nice. She was the best empire

Reviewed on Mar 4, 2026

21C Museum Hotel St Louis
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
$105 nightly
The price is $122 total per night from Mar 29 to Mar 30
$122 total
Mar 29 - Mar 30
Total with taxes and fees
8.8/10 Excellent! (3,112 reviews)
I stayed here in 2025 and made sure to return when in town again. The rooms are great, the price is reasonable, and the free breakfast was outstanding. Also, the parking garage is priced reasonably and I saved a lot of money leaving my car at the hotel and taking the light rail downtown.

Reviewed on Mar 4, 2026

Clayton Plaza Hotel & Extended Stay
See all 1,830 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 $177 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.