Oakland Vacations from $386

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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.
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 $513, price is now $386 per person
$386
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,071 reviews)
A very unique artsy hotel. Had a fantastic stay there. The staff were all so kind and helpful. We got a complimentary upgrade to the Suite Room with a full kitchen. Location is perfect, the Commonwealth restaurant and the roof top bar were amazing. Good food, great drinks and amazing views of the city from the bar. Definitely staying here again.

Reviewed on May 23, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $827, price is now $423 per person
$423
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,649 reviews)
Beautiful hotel, and the parking garage was an unexpected plus. The staff were very friendly and helpful.

Reviewed on May 26, 2026

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Save 100% on your flight
Price was $553, price is now $415 per person
$415
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.4/10 Exceptional! (548 reviews)
Quiet, clean room. Comfortable bedding.

Reviewed on May 24, 2026

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $608, price is now $463 per person
$463
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,006 reviews)
Literary and historical themed hotel, like walking into England. Beautiful decor. We loved it.

Reviewed on May 25, 2026

Budget Inn by Hotel O Greensville I 70

Budget Inn by Hotel O Greensville I 70

2 out of 5
Price was $614, price is now $469 per person
$469
per person
Jul 11 - Jul 18
found 5 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to St. Louis (STL)
6.8/10 (180 reviews)
Super nice people and clean

Reviewed on May 17, 2026

Don't see what you're looking for?
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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
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
Gateway Arch

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

$32
per adult
St. Louis Ghost Tour: Sinister Sins & Shadows
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
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

$29
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
See all activities in Oakland

Oakland Hotel Deals

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
$144 nightly
The price is $169 total per night from May 31 to Jun 1
$169 total
May 31 - Jun 1
Total with taxes and fees
8.6/10 Excellent! (4,083 reviews)
"Taken 3 weeks to get my deposit of $75 to return Back to me. I’ve NEVER experienced this before with any hotel booking."

Reviewed on May 26, 2026

Hyatt Regency St. Louis at The Arch
Hollywood Casino & Hotel St. Louis

Hollywood Casino & Hotel St. Louis

3.5 out of 5
777 Casino Center Drive Maryland Heights MO
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $136 total per night from Jun 1 to Jun 2
$136 total
Jun 1 - Jun 2
Total with taxes and fees
8.4/10 Very Good! (2,212 reviews)
"It was a nice looking hotel I did enjoy the food they had at one of the restaurants"

Reviewed on May 24, 2026

Hollywood Casino & Hotel St. Louis
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

3 out of 5
1088 South Highway Drive Fenton MO
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $115 total per night from May 27 to May 28
$115 total
May 27 - May 28
Total with taxes and fees
7.8/10 Good! (1,301 reviews)
"No way this is a 3 star hotel. The room was small and smelled musty. The window doesn't open, so there's no ventilation. The fan in the bathroom didn't work. The breakfast was a horrible buffet of rubbery scrambled eggs, half cooked sausage links and soupy biscuits and gravy. The staff was VERY nice ..."

Reviewed on May 25, 2026

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham
See all 1,842 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 $386 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.