Oakland Vacations

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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.

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Oakland Hotel Deals

Unique Suites Hotel

Unique Suites Hotel

2.5 out of 5
920 W Lincoln Ave Charleston IL
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $93 total per night from Nov 29 to Nov 30
$93 total
Nov 29 - Nov 30
Total with taxes and fees
8.4/10 Very Good! (708 reviews)
Nice place!

Reviewed on Nov 6, 2025

Unique Suites Hotel
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
$85 nightly
The price is $95 total per night from Dec 4 to Dec 5
$95 total
Dec 4 - Dec 5
Total with taxes and fees
8.6/10 Excellent! (865 reviews)
Microwave, Fridge, Breakfast

Reviewed on Nov 14, 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
$91 nightly
The price is $102 total per night from Nov 30 to Dec 1
$102 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (612 reviews)
Breakfast was wonderful

Reviewed on Nov 15, 2025

Holiday Inn Express Tuscola by IHG
See all 68 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.

Find the Best Oakland Vacation Packages

Oakland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
University Of Illinois Urbana-Champaign Williard Airport (CMI)
Population
880
Max Temp Winter
35ºF
Max Temp Summer
80ºF

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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 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.