Oakland Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

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

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

Find the Best Oakland Vacation Packages

Oakland Hotel Deals

Pressey House Lakeside Bed & Breakfast
Pressey House Lakeside Bed & Breakfast
3 out of 5
32 Belgrade Rd, Oakland, ME
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Pressey House Lakeside Bed & Breakfast
Maine Evergreen Hotel, Ascend Hotel Collection
Maine Evergreen Hotel, Ascend Hotel Collection
2.5 out of 5
65 Whitten Rd, Augusta, ME
Fully refundableReserve now, pay when you stay
The price is ₩274,055 per night from Jul 14 to Jul 15
₩274,055
₩298,720 total
Jul 14 - Jul 15
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"Excellent"

Reviewed on Jul 9, 2025

Maine Evergreen Hotel, Ascend Hotel Collection
Fireside Inn & Suites Waterville
Fireside Inn & Suites Waterville
2 out of 5
376 Main Street, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is ₩224,684 per night from Jul 14 to Jul 15
₩224,684
₩244,905 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (999 reviews)
"Nice place to stay. Pool and hot tub were excellent. We'd stay again"

Reviewed on Jul 8, 2025

Fireside Inn & Suites Waterville
See all 535 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.

Frequently asked questions

How much does an Oakland vacation package cost?
You'll find cheap prices on Expedia for your Oakland break. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
To score cheap Oakland vacation packages, plan your trip outside of peak periods such as public holidays. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Oakland?
Generally, a handful of days is enough to visit the major sights during your Oakland vacation. However, if you prefer to have time to rest or take day trips, consider extending your trip.
How to find the best Oakland package deals?
Start your search for an Oakland package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Oakland package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oakland escape underway.
Is it cheaper to book an Oakland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Oakland vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Oakland?
If you have your Oakland vacation dates finalized, book as soon as you can to grab some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Oakland?

  1. Choose when to go: Check your calendar and get your bags packed. Your favorite season and the type of activities available will also help you decide when to visit Oakland.
  2. Set a budget: Consider costs such as flights, meals and transportation when working out how much to put aside for your trip to Oakland. Then, pick a property that fits your budget, whether that's an economical option or a deluxe retreat.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to experience in Oakland. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels 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.