Oakland Vacation Packages

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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.

Top Oakland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Wingate by Wyndham St. Louis Airport

Wingate by Wyndham St. Louis Airport

2.5 out of 5
per person
Sep 11 - Sep 15
found 20 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to St. Louis (STL)
9.4/10 Exceptional! (1,353 reviews)
Great last minute booking. Close to airport.

Reviewed on Aug. 2, 2025

The Cheshire

The Cheshire

4 out of 5
per person
Sep 11 - Sep 15
found 20 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
This is definitely a unique hotel. The book/author themes is kind of cool, but overall it felt very outdated. The giant bear in the lounge area looks like it's been there for 100 years...missing fingers and toes...very dusty. Pool area could be really great if they had less metal tables and more loungers. Breakfast was a bonus.

Reviewed on Aug. 1, 2025

DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
per person
Sep 11 - Sep 15
found 20 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Beautiful property, pleasant and responsive staff, delicious warm cookies! And convenient location near city hall and police department.

Reviewed on Jul. 27, 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
per person
Oct 23 - Oct 27
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.4/10 Very Good! (1,003 reviews)
Great food options. Lots to do for a family and a couple on a date night.

Reviewed on Aug. 2, 2025

Hilton St. Louis Airport

Hilton St. Louis Airport

3.5 out of 5
Woodson Terrace
per person
Oct 23 - Oct 27
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
7.6/10 Good! (1,005 reviews)
The pool was broken and had to be maintenance

Reviewed on Jul. 24, 2025

Ready to book your vacation to Oakland?

 

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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
The price is CA $139 per night from Aug 22 to Aug 23
CA $139
CA $164 total
Aug 22 - Aug 23
includes taxes & fees
8.4/10 Very Good! (3,895 reviews)
"Great Hotel, Great Staff!"

Reviewed on Aug. 1, 2025

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
The price is CA $152 per night from Aug 3 to Aug 4
CA $152
CA $198 total
Aug 3 - Aug 4
includes taxes & fees
8.2/10 Very Good! (2,025 reviews)
"It was very nice"

Reviewed on Aug. 2, 2025

Hollywood Casino & Hotel St. Louis
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
The price is CA $165 per night from Sep 2 to Sep 3
CA $165
CA $193 total
Sep 2 - Sep 3
includes taxes & fees
9.4/10 Exceptional! (2,898 reviews)
"Affordable and very near Busch stadium. The included meals were nice."

Reviewed on Aug. 1, 2025

Drury Plaza Hotel St. Louis at the Arch
See all 1,738 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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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 great live music or attend a baseball game.

Busch Stadium
Gateway Arch featuring modern architecture, a city and a skyscraper

Gateway Arch

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

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: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

CA $31
per adult
96% of travellers recommend
St Louis: City Museum General Admission Ticket
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

CA $33
per adult
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
St Louis: 75-Minute City Trolley Tour

St Louis: 75-Minute City Trolley Tour

CA $41
per adult
St Louis: 75-Minute City Trolley Tour
See all activities in Oakland

Frequently asked questions

How much does an Oakland vacation package cost?
Offering great value package deals from CA $675 on Expedia, you'll be pleasantly surprised at how much a vacation to Oakland costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Oakland?
If you're hoping to snag a cheap Oakland vacation package, consider visiting in January, February and November. You're likely to find lower prices on airfares and hotels during these quieter months — perfect for a budget-friendly break.
How many days is enough for Oakland?
Oakland vacations come in various shapes and sizes, but to really get a feel for this place, we'd suggest 2 days is about right. In this timeframe, you can visit headline attractions like Museum of Transportation and Laumeier Sculpture Park along with lesser-known gems. Don't skip cool areas such as Downtown Clayton and Richmond Heights either. If you're clever with your time, you can even allow for a day trip or two from Oakland too.
How to find the best Oakland package deals?
Landing a cheap Oakland package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply some filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most affordable Oakland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an Oakland vacation as a package?
You can enjoy significant savings on your Oakland getaway by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Oakland?
If you're planning a spontaneous Oakland vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Oakland?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Oakland.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and dining out to activities and flights. Your hotel will likely be the largest expense during your trip to Oakland.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Oakland. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a tailored Oakland vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.