Oakland Vacations from $694
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Oakland Vacation
Our vacation packages to Oakland give you endless opportunities to discover new sights, sounds and experiences. And with all of the travel arrangements taken care of, you'll be free to enjoy your city getaway without a worry in the world. During your trip to Oakland, give yourself plenty of time for sightseeing. A fantastic place to start exploring is Walnut Point State Park. Don't put off exploring this city any longer. Your dream Oakland vacation is a few clicks away with Expedia.
The Latest Oakland Vacation Packages
- Motel 6 Urbana, IL
Dec 24 - Dec 28Motel 6 Urbana, IL + Flight
Urbana4 nights2.0 star property8.0/10 - Very good (811 reviews)Roundtrip • Philadelphia (PHL) - Champaign (CMI)PHL - CMI • 1 stop CMI - PHL • 1 stop$749$694found 23 hours agoper traveler - Champaign Garden Inn
Dec 24 - Dec 28Champaign Garden Inn + Flight
Champaign4 nights3.0 star property9.8/10 - Exceptional (609 reviews)Roundtrip • Philadelphia (PHL) - Champaign (CMI)PHL - CMI • 1 stop CMI - PHL • 1 stop$854$759found 23 hours agoper traveler - I Hotel And Illinois Conference Center
Dec 24 - Dec 28I Hotel And Illinois Conference Center + Flight
Champaign4 nights4.0 star property9.8/10 - Exceptional (2,293 reviews)"Clean room and free parking"Reviewed November 11, 2026Roundtrip • Philadelphia (PHL) - Champaign (CMI)PHL - CMI • 1 stop CMI - PHL • 1 stop$968$897found 23 hours agoper traveler - Illini Inn & Suites Hotel - Rantoul/Gifford/Champaign/Urbana
Dec 24 - Dec 28Illini Inn & Suites Hotel - Rantoul/Gifford/Champaign/Urbana + Flight
Rantoul4 nights2.0 star property8.8/10 - Excellent (571 reviews)"Enjoyed the friendly service, breakfast was tremendous"Reviewed November 11, 2026Roundtrip • Philadelphia (PHL) - Champaign (CMI)PHL - CMI • 1 stop CMI - PHL • 1 stop$754$710found 23 hours agoper traveler - Red Lion Inn & Suites Urbana
Dec 24 - Dec 28Red Lion Inn & Suites Urbana + Flight
Urbana4 nights2.5 star property6.4/10 - (42 reviews)"The tv’s were tiny and the signal sucked. The channels were in and out the whole time we were there."Reviewed November 9, 2026Roundtrip • Philadelphia (PHL) - Champaign (CMI)PHL - CMI • 1 stop CMI - PHL • 1 stop$785$746found 23 hours agoper traveler
Where to stay near Oakland
Charleston
For family travelers seeking a memorable trip, Charleston offers a blend of educational and recreational experiences perfect for all ages. Visitors can explore the vibrant campus of Eastern Illinois University, enjoy the historical charm of the Lincoln Log Cabin, and unwind at the Lantz Arena. Located about 15 miles by car from Oakland, Charleston provides easy access to outdoor adventures and cultural attractions, making it a smart choice for your hotel stay.
Hindsboro
Experience the charm of Hindsboro, an excellent hub for travelers seeking a blend of business, family fun, and nature. Just a short distance from Oakland, this city invites you to explore attractions like Walnut Point State Park, Eastern Illinois University, and the unique Hippie Memorial. With a steady flow of visitors year-round, Hindsboro is a smart choice for your stay, offering a welcoming atmosphere and easy access to local highlights.
Brocton
Make your vacation planning effortless by staying in Brocton, a haven for outdoor enthusiasts and families seeking adventure and scenery. With attractions like Walnut Point State Park, Eastern Illinois University, and the Edgar County Fairgrounds nearby, Brocton offers a delightful blend of nature and local culture. Located about 7 miles from Oakland, this charming city provides easy access to recreational activities year-round, making it a smart choice for your next getaway.
Ashmore
Ashmore stands out as a prime spot for travelers interested in outdoor adventures and scenic experiences. Visitors can explore the beautiful national state park, relax by the lake, or enjoy the lush forests nearby. Popular attractions such as Eastern Illinois University and the historic Airtight Bridge provide unique insights into the area’s culture and history. Located about 8 miles from Oakland, Ashmore is a smart choice for a memorable getaway, offering a blend of recreation and relaxation all year round.
Kansas
Travelers seeking a weekend getaway will find Kansas to be the ideal base for their vacation, featuring an array of outdoor and eco-friendly experiences. With attractions like the nature reserve and the beautiful Walnut Point State Park, visitors can immerse themselves in nature, while Eastern Illinois University adds a vibrant educational atmosphere. Located about 8 miles from Oakland, Kansas offers easy access to adventure and relaxation. For a memorable stay, Kansas is a smart hotel booking choice.
Oakland Hotel Deals
Green Mill Village Hotel & Suites, BW Signature Collection
Green Mill Village Hotel & Suites, BW Signature Collection"Great experience!"
Holiday Inn Express Tuscola by IHG
Holiday Inn Express Tuscola by IHG"CLEAN AND QUIET. CLOSE TO CONVIENCES AND THE HIGHWAY. STAFF WERE HELPFUL AND COURTEOUS. WOULD STAY HERE AGAIN WHEN I RETURN TO TUSCOLA."
"See my previous review. No working heat. No working T.V. Hotel bar closed on a Saturday night during parents weekend at EIU. Addressed the concerns with the staff with a whole day to fix the issues. Nothing got fixed. Paid full price. We will be staying somewhere else next time."
"Best Hampton Inn ever!"
"Great"
Charleston House Bed & Breakfast Inn
Charleston House Bed & Breakfast Inn
"If you need a clean room for a night or two, the Inn will work. As soon as you check in, take a quick look at the shampoo/conditioner dispensers to make sure there is enough content; why because they are squeezable bottles, if they are too low; you won't get any shampoo. Simply call down and let them know. The breakfast is listed as Continental, and that is exactly what it is. They do have a waffle maker, the oatmeal is instant; no hot ready made food. As long as you know ahead of time,...
Frequently Asked Questions
How much does an Oakland vacation package cost?
You can grab a vacation package to this top destination from $694 on Expedia. However, how much your vacation to Oakland costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Oakland?
If you're looking to book a cheap Oakland vacation package, consider traveling in November, December and January. You'll usually find better prices on hotels and flights during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Oakland?
With a well-organized schedule, you can easily tick off the top Oakland sights in a few days. But if you prefer to discover hidden gems or go on day tours, think about booking your Oakland vacation for longer.
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," "Traveler 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 vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can personalize 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 vacation 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.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
If you're like us, you love going away but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Oakland vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.