Oakland Vacations

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Find the Best Oakland Vacation Packages

Oakland Hotel Deals

Best Western Heartland Inn

Best Western Heartland Inn

2.5 out of 5
1416 Broadway Avenue East Mattoon IL
Fully refundableReserve now, pay when you stay
The price is ₩130,646 per night from Jul 26 to Jul 27
₩130,646
₩146,297 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very Good! (616 reviews)
"The property was clean and staff friendly. My problem was the water didn’t get hot for the shower, everything in my room was leaning and the drawer to the chest wouldn’t stay closed."

Reviewed on Jul 20, 2026

Best Western Heartland Inn
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 ₩109,291 per night from Aug 11 to Aug 12
₩109,291
₩122,384 total
Aug 11 - Aug 12
includes taxes & fees
Baymont by Wyndham Tuscola
Comfort Suites Mattoon East

Comfort Suites Mattoon East

2.5 out of 5
1408 Broadway Ave E Mattoon IL
Fully refundable
The price is ₩136,927 per night from Aug 20 to Aug 21
₩136,927
₩153,331 total
Aug 20 - Aug 21
includes taxes & fees
8.8/10 Excellent! (984 reviews)
"I have stayed here before, and have overall found it to be a great place. However, I couldn’t get WiFi, and television reception was not good."

Reviewed on Jul 22, 2026

Comfort Suites Mattoon East
See all 53 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.

Stay near popular Oakland attractions

Walnut Point State Park

8.0/10 (1 review)
You can take time to visit Walnut Point State Park during your travels to Oakland.
See properties

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?
January, February and November are the best times to look for cheap Oakland vacation packages. Opting to travel in quieter periods means you can typically find lower prices on flights and hotels.
How many days is enough for Oakland?
Usually, a handful of days is enough to check out the major attractions during your Oakland vacation. However, if you want to have more time to kick back or take day trips, think about extending your itinerary.
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.
How to plan a trip to Oakland?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Oakland.
  2. Figure out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and flights. Your accommodations will likely be the biggest expense during your trip to Oakland.
  3. Decide how long to go away for: Now that you're up to speed on Oakland, you can figure out the right length of your break. Create a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in order, 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.