Oakland Vacations from $626

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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.

The Latest Oakland vacation packages

Price found within the past 48 hours. Click for updated prices.
First Heritage Inn Rantoul
Motel 6 Urbana, IL
La Quinta Inn by Wyndham Champaign
Rodeway Inn Urbana Champaign University Area
Super 8 by Wyndham Tuscola
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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
$87 nightly
The price is $98 total per night from Sep 4 to Sep 5
$98 total
Sep 4 - Sep 5
Total includes taxes and fees
8.6/10 Excellent! (791 reviews)
"Nice"

Reviewed on Aug 12, 2025

Comfort Suites Mattoon East
Holiday Inn Express Tuscola by IHG

Holiday Inn Express Tuscola by IHG

2.5 out of 5
1201 Tuscola Blvd, Tuscola, IL
Fully refundable
$104 nightly
The price is $116 total per night from Sep 1 to Sep 2
$116 total
Sep 1 - Sep 2
Total includes taxes and fees
8.8/10 Excellent! (584 reviews)
"Older but very clean nice pool great staff"

Reviewed on Aug 18, 2025

Holiday Inn Express Tuscola by IHG
Unique Suites Hotel

Unique Suites Hotel

2.5 out of 5
920 W Lincoln Ave, Charleston, IL
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $113 total per night from Aug 27 to Aug 28
$113 total
Aug 27 - Aug 28
Total includes taxes and fees
8.4/10 Very Good! (670 reviews)
Cool place in Charleston.
"Other than the fact that there was an all day kids birthday party at the pool the one day we planned to chill and swim, I have zero complaints. The room was clean, the staff was friendly and helpful and I will definitely book there again."

Reviewed on Aug 18, 2025

Unique Suites Hotel
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.

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Frequently asked questions

How much does an Oakland vacation package cost?
You can grab a vacation package to this top destination from $626 on Expedia. However, how much your vacation to Oakland costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Oakland?
If you're looking to book a cheap Oakland vacation package, consider traveling in November, December and January. You'll usually find better prices on hotels and flights during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Oakland?
With a well-organized schedule, you can easily tick off the top Oakland sights in a few days. But if you prefer to discover hidden gems or go on day tours, think about booking your Oakland vacation for longer.
How to find the best Oakland package deals?
Landing a cheap Oakland package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Oakland package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can personalize your Oakland getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Oakland?
Land amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Oakland getaway.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
If you're like us, you love going away but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Oakland vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.