Oakland Vacations from $256

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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.
Crowne Plaza St. Louis Airport by IHG

Crowne Plaza St. Louis Airport by IHG

3.5 out of 5
Price was $352, price is now $256 per person
$256
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8/10 Very Good! (1,005 reviews)
Perfect hotel for my three day trip! Nice breakfast buffet, gym and overall ambience. Rooms could use some updating as they have not been remodeled in several years. I would definitely stay again.

Reviewed on Sep 27, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $474, price is now $305 per person
$305
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,581 reviews)
Visited to do some writing. Staff was friendly and helpful, all amenities were clean and functional. Wildwood area is pretty quiet after 8.

Reviewed on Oct 5, 2025

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Price was $428, price is now $294 per person
$294
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,005 reviews)
This is a wonderful hotel. The staff are incredibly helpful and courteous. The temp in the room was easily adjustable, the shower was spacious, and the bed comfortable. The decor in the different colored rooms was so fun. I had the green room and felt as if I landed in the Emerald City. Spectacular visit - thanks Angad!

Reviewed on Oct 8, 2025

The Cheshire

The Cheshire

4 out of 5
Price was $413, price is now $299 per person
$299
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.6/10 Excellent! (1,003 reviews)
Cute place. A/c in room could have worked better

Reviewed on Oct 5, 2025

Hampton Inn By Hilton St Louis Airport

Hampton Inn By Hilton St Louis Airport

2.5 out of 5
Woodson Terrace
Price was $422, price is now $308 per person
$308
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (62 reviews)
All areas was kept clean and breakfast options was great

Reviewed on Oct 4, 2025

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Discover the most popular places to visit in Oakland

Busch Stadium

Busch Stadium

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

Busch Stadium
St. Louis Union Station

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
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

The Dinner Detective Murder Mystery Dinner Show - St. Louis

Dinner Detective True Crime Murder Mystery Show - St. Louis, MO

$89
per adult
Dinner Detective True Crime Murder Mystery Show - St. Louis, MO
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
Step into the shadows and discover the haunting tales of our city's past.

St. Louis Ghosts: Gateway Ghouls and Hauntings

$32
per adult
100% of travellers recommend
St. Louis Ghosts: Gateway Ghouls and Hauntings
See all activities in Oakland

Oakland Hotel Deals

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
$103 nightly
The price is $120 total per night from Oct 19 to Oct 20
$120 total
Oct 19 - Oct 20
Total with taxes and fees
8.8/10 Excellent! (2,949 reviews)
"The breakfast is alot like other hot breakfast in hotels but you eat in the restaurant in better surroundings."

Reviewed on Oct 3, 2025

Clayton Plaza Hotel & Extended Stay
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
$136 nightly
The price is $159 total per night from Oct 19 to Oct 20
$159 total
Oct 19 - Oct 20
Total with taxes and fees
9.4/10 Exceptional! (3,106 reviews)
"Great views of the Arch from their 8th floor terrace!! Having free breakfast and dinner with drinks was nice. Customer service was a bit lacking. We asked for blankets twice before we were able to get them the next day and housekeeping didn't come into our room even though we said yes we wanted them ..."

Reviewed on Oct 7, 2025

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
$122 nightly
The price is $144 total per night from Nov 2 to Nov 3
$144 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (3,986 reviews)
"Felt clean, just a bit of a damp odor."

Reviewed on Oct 5, 2025

Hyatt Regency St. Louis at The Arch
See all 1,711 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.

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 $256 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.