Oakland Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Oakland

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 2.218.026 ₫ per night from 1 Sept to 2 Sept
2.218.026 ₫
2.483.746 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (796 reviews)
"Clean with nice pool and hot tub. Great breakfast choices"

Reviewed on 24 Aug 2025

Comfort Suites Mattoon East
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 2.965.275 ₫ per night from 29 Aug to 30 Aug
2.965.275 ₫
3.387.530 ₫ total
29 Aug - 30 Aug
includes taxes & fees
8.4/10 Very Good! (673 reviews)
"Close to EIU and restaurant on site is open and convient"

Reviewed on 22 Aug 2025

Unique Suites Hotel
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 1.921.498 ₫ per night from 31 Aug to 1 Sept
1.921.498 ₫
2.151.694 ₫ total
31 Aug - 1 Sept
includes taxes & fees
7.6/10 Good! (553 reviews)
"Check in was flawless. The attendant was knowledgeable, courteous, thorough and friendly. The lobby was clean. The room was clean. We haven’t experienced the pool yet but it looks clean. My ONLY criticism so far is the hotel needs to be updated, it is old and out of date…"

Reviewed on 23 Aug 2025

Baymont 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.