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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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Oakland

Suite Dreams Hotel
Suite Dreams Hotel
2.5 out of 5
300 Broadway Avenue East, Mattoon, IL
Fully refundableReserve now, pay when you stay
7.2/10 Good! (473 reviews)
"Great"

Reviewed on 3 Jun, 2025

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Suite Dreams Hotel
Comfort Suites Mattoon
Comfort Suites Mattoon
2.5 out of 5
1408 Broadway Ave E, Mattoon, IL
Fully refundableReserve now, pay when you stay
The price is S$134 per night from 26 Jun to 27 Jun
S$134
26 Jun - 27 Jun
includes taxes & fees
8.6/10 Excellent! (758 reviews)
"The hotel was nice and clean. The staff was nice and courteous. There was plenty of places to eat and shop in the immediate area."

Reviewed on 21 Jun, 2025

Comfort Suites Mattoon
Super 8 by Wyndham Tuscola
Super 8 by Wyndham Tuscola
2 out of 5
1007 E Southline Dr, Tuscola, IL
Fully refundableReserve now, pay when you stay
The price is S$86 per night from 6 Jul to 7 Jul
S$86
6 Jul - 7 Jul
includes taxes & fees
7.6/10 Good! (567 reviews)
"Wonderful property, well kept, and very friendly and helpful staff. Would definitely stay here again!"

Reviewed on 17 Jun, 2025

Super 8 by Wyndham Tuscola
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.