Oakland Vacation Packages

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Your Oakland Vacation

Our vacation packages to Oakland give you endless opportunities to discover new sights, sounds and experiences. And with all of the travel arrangements taken care of, you'll be free to enjoy your city getaway without a worry in the world. During your trip to Oakland, give yourself plenty of time for sightseeing. A fantastic place to start exploring is Walnut Point State Park. Don't put off exploring this city any longer. Your dream Oakland vacation is a few clicks away with Expedia.

Ready to book your vacation to Oakland?

 

Choose your dates

Oakland Hotel Deals

Comfort Suites Mattoon East

Comfort Suites Mattoon East

2.5 out of 5
1408 Broadway Ave E, Mattoon, IL
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from Sep 1 to Sep 2
CA $116
CA $130 total
Sep 1 - Sep 2
includes taxes & fees
Comfort Suites Mattoon East
Unique Suites Hotel

Unique Suites Hotel

2.5 out of 5
920 W Lincoln Ave, Charleston, IL
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Sep 2 to Sep 3
CA $135
CA $155 total
Sep 2 - Sep 3
includes taxes & fees
Unique Suites Hotel
Baymont by Wyndham Tuscola

Baymont by Wyndham Tuscola

2.5 out of 5
1006 Southline Road, Tuscola, IL
Fully refundableReserve now, pay when you stay
The price is CA $100 per night from Sep 21 to Sep 22
CA $100
CA $112 total
Sep 21 - Sep 22
includes taxes & fees
7.6/10 Good! (554 reviews)
"Great property for a 2 star hotel"

Reviewed on Aug. 25, 2025

Baymont by Wyndham Tuscola
See all 64 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 season, length of stay and your choice of hotel will determine how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
If you'd like to score a cheap Oakland vacation package, consider travelling in January, February and November. You're likely to find lower prices on flights and accommodations during these months — perfect for a budget-friendly getaway.
How many days is enough for Oakland?
Generally, a handful of days is enough to explore the top sights during your Oakland vacation. But if you'd like to have some time to kick back or take day trips, think about extending your trip.
How to find the best Oakland package deals?
Finding a cheap Oakland package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Oakland package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book an Oakland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Oakland vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Oakland?
If you've got your Oakland vacation dates confirmed, book as early as you can to snap up some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Oakland?

  1. Choose your travel dates: The things you plan to do in Oakland and your preferred season will help you decide when to go.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to put aside for your trip to Oakland. Then, pick a property that suits your budget, whether that's an economical stay or a more luxurious retreat.
  3. Work out your trip length: Consider how much time you want to spend exploring Oakland. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose an Oakland vacation package that brings all your bookings together.

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