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.

Top Oakland vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Jan 8 - Jan 10

    The Wildwood Hotel + Flight

    Wildwood
    2 nights
    3.5 star property
    9.2/10 - Wonderful (1,679 reviews)
    "The hotel is beautiful; we felt like we were in Europe! The room was lovely and very clean. The staff was very friendly and helpful. The location was great too, close to shopping and restaurants, walkable, felt very safe, and near a park. Having a parking garage free of charge was also great! We would definitely stay again."
    Reviewed November 5, 2026
    Roundtrip • Buffalo (BUF) - St. Louis (STL)
    BUF - STL • 1 stop STL - BUF • 1 stop
    CA $961
    CA $689
    per traveller
    found 1 day ago
    The Wildwood Hotel
  • Dec 16 - Dec 20

    Holiday Inn St. Louis Arpt West-Earth City by IHG + Flight

    Earth City
    4 nights
    3.5 star property
    7.6/10 - Good (1,000 reviews)
    "It was clean and have no complaints."
    Reviewed November 3, 2026
    Roundtrip • Calgary (YYC) - St. Louis (STL)
    YYC - STL • 1 stop STL - YYC • 2 stops
    CA $1,199
    CA $1,074
    per traveller
    found 4 hours ago
    Holiday Inn St. Louis Arpt West-Earth City by IHG
  • Dec 16 - Dec 20

    Ameristar Casino Resort and Spa + Flight

    St. Charles
    4 nights
    4.5 star property
    8.6/10 - Excellent (1,091 reviews)
    "The staff was wonderful and we had a great night"
    Reviewed November 5, 2026
    Roundtrip • Calgary (YYC) - St. Louis (STL)
    YYC - STL • 1 stop STL - YYC • 2 stops
    CA $1,656
    CA $1,483
    per traveller
    found 4 hours ago
    Ameristar Casino Resort and Spa
  • Dec 16 - Dec 20

    Crowne Plaza St. Louis Airport by IHG + Flight

    Bridgeton
    4 nights
    3.5 star property
    8.0/10 - Very good (1,000 reviews)
    Roundtrip • Calgary (YYC) - St. Louis (STL)
    YYC - STL • 1 stop STL - YYC • 2 stops
    CA $1,194
    CA $1,091
    per traveller
    found 4 hours ago
    Crowne Plaza St. Louis Airport by IHG
  • Dec 16 - Dec 20

    The Westin St. Louis + Flight

    Downtown St. Louis
    4 nights
    4.5 star property
    8.6/10 - Excellent (1,000 reviews)
    "Great place to stay if you want to be right down in the middle of all the action! Orlando our valet was amazing!!"
    Reviewed November 3, 2026
    Roundtrip • Calgary (YYC) - St. Louis (STL)
    YYC - STL • 1 stop STL - YYC • 2 stops
    CA $1,337
    CA $1,226
    per traveller
    found 4 hours ago
    The Westin St. Louis

Discover the most popular places to visit in Oakland

Oakland Hotel Deals

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.

Frequently Asked Questions

How much does an Oakland vacation package cost?

Offering great value package deals from CA $689 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.