Oakland Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

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

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 SARĀ 316 per night from Jul 19 to Jul 20
SARĀ 316
SARĀ 354 total
19 Jul - 20 Jul
includes taxes & fees
8.2/10 Very Good! (612 reviews)
"Hot water in the shower lasted 2 minutes the first day and 7 minutes the second day."

Reviewed on 15 July 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 SARĀ 275 per night from Jul 22 to Jul 23
SARĀ 275
SARĀ 307 total
22 Jul - 23 Jul
includes taxes & fees
7.6/10 Good! (638 reviews)
"Good spot Nothing special Just solid"

Reviewed on 10 July 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 SARĀ 252 per night from Jul 27 to Jul 28
SARĀ 252
SARĀ 282 total
27 Jul - 28 Jul
includes taxes & fees
7.4/10 Good! (729 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 July 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 vacation package cost?
You'll find cheap prices on Expedia for your Oakland break. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
If you'd like to score a cheap Oakland vacation package, consider traveling in January, February and November. You're likely to find lower prices on flights and accommodations during these months ā€” perfect for a budget-friendly getaway.
How to find the best Oakland package deals?
Finding a cheap Oakland package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Oakland package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book an Oakland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Oakland vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Oakland?
If you've got your Oakland vacation dates confirmed, book as early as you can to snap up some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Oakland?

  1. Choose your travel dates: The things you plan to do in Oakland and your preferred season will help you decide when to go.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to put aside for your trip to Oakland. Then, pick a property that suits your budget, whether that's an economical stay or a more luxurious retreat.
  3. Work out your trip length: Consider how much time you want to spend exploring Oakland. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose an Oakland vacation package that brings all your bookings together.