Oakland Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Oakland

Holiday Inn Express Tuscola by IHG

Holiday Inn Express Tuscola by IHG

2.5 out of 5
1201 Tuscola Blvd, Tuscola, IL
Fully refundable
The price is S$149 per night from 14 Sept to 15 Sept
S$149
14 Sept - 15 Sept
includes taxes & fees
8.8/10 Excellent! (583 reviews)
"Great place clean big room great location next to I57 restaurants walking distance"

Reviewed on 4 Aug, 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
The price is S$153 per night from 24 Aug to 25 Aug
S$153
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (665 reviews)
Just what we needed
"Overall me & my family enjoyed our stay. The AC wasn’t as strong as we would have liked & the bed was smaller than I imagined. It was soo hot in the lobby & we had to wait to check in. But the pool was really nice & the property was well kept. I would stay again."

Reviewed on 27 Jul, 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
The price is S$126 per night from 3 Sept to 4 Sept
S$126
3 Sept - 4 Sept
includes taxes & fees
8.6/10 Excellent! (790 reviews)
"Nice"

Reviewed on 12 Aug, 2025

Comfort Suites Mattoon East
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.

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.