Oakland Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.

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 $188 per night from Aug 28 to Aug 29
CA $188
per night
Aug 28 - Aug 29
8.6/10 Excellent! (4,158 reviews)
"Great"

Reviewed on Aug 3, 2026

Hyatt Regency St. Louis at The Arch
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
The price is CA $130 per night from Aug 30 to Aug 31
CA $130
per night
Aug 30 - Aug 31
9/10 Wonderful! (3,311 reviews)
"Room was clean and spacious. There was a faint odor to the room but I know recent work was done on the pool, as it smelled like it was close by."

Reviewed on Aug 3, 2026

Clayton Plaza Hotel & Extended Stay
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 $182 per night from Aug 16 to Aug 17
CA $182
per night
Aug 16 - Aug 17
8.6/10 Excellent! (2,186 reviews)
"Excellent service"

Reviewed on Aug 3, 2026

Hollywood Casino & Hotel St. Louis
See all 1,954 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
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Stay near popular Oakland attractions

Grant's Trail - Backstopper's Park Trailhead

You can take time to visit Grant's Trail - Backstopper's Park Trailhead during your travels to Oakland.
See properties

What to do in Oakland

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

CA $34
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
The Gateway Arch National Park & Museum

StL's Signature "Sights and Bites" - Private Tour in St. Louis

CA $246
per adult
StL's Signature "Sights and Bites" - Private Tour in St. Louis
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

CA $35
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
See all activities in Oakland

Frequently asked questions

How much does an Oakland vacation package cost?
Offering great value package deals 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.