Oakland Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Oakland

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 2.080.505 ₫ per night from 16 Jul to 17 Jul
2.080.505 ₫
2.329.749 ₫ total
16 Jul - 17 Jul
includes taxes & fees
8.2/10 Very good! (611 reviews)
"Great place and good price!"

Reviewed on 11 Jul 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 1.942.593 ₫ per night from 21 Jul to 22 Jul
1.942.593 ₫
2.175.316 ₫ total
21 Jul - 22 Jul
includes taxes & fees
7.6/10 Good! (638 reviews)
"Good spot Nothing special Just solid"

Reviewed on 10 Jul 2026

Baymont by Wyndham Tuscola
Super 8 by Wyndham Mattoon

Super 8 by Wyndham Mattoon

2 out of 5
205 Mcfall Rd Mattoon IL
Fully refundableReserve now, pay when you stay
The price is 1.763.963 ₫ per night from 30 Jul to 31 Jul
1.763.963 ₫
1.975.286 ₫ total
30 Jul - 31 Jul
includes taxes & fees
7.4/10 Good! (728 reviews)
"Well it was not exactly the feeli g of clean and comfortable that I was going for it had stained blankets the floor had stains the shower had no bar to hold my rag the drain fell apart and becsme detached from the tub the shower head fell off the water was really hot I did get burnt when above all ..."

Reviewed on 11 Jul 2026

Super 8 by Wyndham Mattoon
See all 51 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 holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday 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 holiday 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 holiday. 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," "Traveller 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 holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can personalise 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 holiday 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 accommodation 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 personalised Oakland holiday package.

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