Oakland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave 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.
Top Oakland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Cheshire
CA $1,205
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,004 reviews)
Charming and quaint alternative to a Holiday Inn. It was renovated 10-15 years ago but not much care since then. The pool was allegedly open still (mid September) but when we looked out to go use it, there was debris in it and it wasn’t very inviting. The price was affordable and it was pet friendly, I only wish we could have experienced it during its heyday years ago when it was properly maintained and cleaned.
Reviewed on Sep 17, 2026
Ready to book your vacation to Oakland?
Oakland Hotel Deals
Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
CA $132
CA $154 total
Oct 4 - Oct 5
includes taxes & fees
8.8/10 Excellent! (3,406 reviews)
"I would not stay at this hotel again. We were there for three days and they did not make the beds. There is no maid service."
Reviewed on Sep 18, 2026
Hyatt Regency St. Louis at The Arch
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
CA $213
CA $251 total
Oct 1 - Oct 2
includes taxes & fees
8.6/10 Excellent! (4,287 reviews)
"I would recommend going somewhere else"
Reviewed on Sep 18, 2026
Pear Tree Inn St. Louis Airport
10810 Pear Tree Ln St. Ann MO
Fully refundableReserve now, pay when you stay
CA $126
CA $148 total
Oct 12 - Oct 13
includes taxes & fees
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.
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.
What to do in Oakland
St. Louis Ghost Tour: Sinister Sins & Shadows
CA $33
per adult
100% of travellers recommend
StL's Signature "Sights and Bites" - Private Tour in St. Louis
CA $242
per adult
Lemp Haunted Neighborhood Walking Tour
CA $35
per adult
84% of travellers recommend
Frequently asked questions
How much does an Oakland vacation package cost?
Offering great value package deals from CA $1,047 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?
- 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.
- 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.
- 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.
- 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.
