A lake surrounded by trees with autumn leaves.

Oakland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Oakland Vacation

There's no better way to embark on an adventure than with one of our vacation packages to Oakland. The rich history and eclectic style are just a couple of the convincing reasons to visit this captivating city. Make your trip to Oakland even more fun and exciting by going sightseeing. Colby College, Belgrade Lakes Chain and Waterville Opera House are among the leading attractions worth exploring. Expedia can help you escape the everyday. Tailor your vacation to Oakland to match your travel style, whatever that may look like.

Top Oakland vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Dec 10 - Dec 13

    The Brunswick Hotel + Flight

    Brunswick
    3 nights
    3.0 star property
    9.4/10 - Exceptional (1,006 reviews)
    Roundtrip • Toronto (YTZ) - Augusta (AUG)
    YTZ - PWM • 2 stops PWM - YTZ • 1 stop
    CA $1,331
    CA $1,278
    per traveller
    found 17 hours ago
    The Brunswick Hotel

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?

You'll find cheap prices from CA $1,278 on Expedia for your Oakland escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Oakland costs.

What are the cheapest months to go to Oakland?

The off-season is the best time to travel to Oakland if you're on a budget. Another tip for getting cheap Oakland vacation packages? Avoid visiting during public holidays and any major events.

How many days is enough for Oakland?

For your Oakland vacation, a handful of days will be enough to tour the top spots. Be sure to check out Common Street Arts — it's one of the leading sights in this destination. If you're looking for more adventure, consider basing yourself here and heading off on some tours from Oakland.

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 "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Oakland package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oakland getaway 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 money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component individually. And you'll still get the freedom to create a tailored Oakland vacation by choosing your favourite accommodation type, airline and car class.

When to book a vacation package to Oakland?

Secure amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Oakland trip.

How to plan a trip to Oakland?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favourite time of year and the activities available will also help you decide when to vacation in Oakland.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Oakland. Then, select a hotel that fits your budget, whether that's an affordable stay or a deluxe getaway.
  3. Set the duration of your trip: Start by listing all the activities and sights you want to experience in Oakland. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Oakland vacation package.

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