Oakland Vacations from $420

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The Latest Oakland vacation packages

Price found within the past 48 hours. Click for updated prices.
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Stay Pittsburgh
The Oaklander Hotel, Autograph Collection
Placemakr Downtown Pittsburgh at The Pennsylvanian
Traveler's Rest Hotel
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Oakland Hotel Deals

Holiday Inn Youngstown South by IHG

Holiday Inn Youngstown South by IHG

3 out of 5
7410 South Ave Boardman OH
Fully refundable
$109 nightly
The price is $126 total per night from Jun 14 to Jun 15
$126 total
Jun 14 - Jun 15
Total with taxes and fees
8.6/10 Excellent! (751 reviews)
"Wallpaper torn in bathroom by toilet paper roll. Shower curtain was coming off the wall. Reading lights had wires sticking out with no light attached. Bathroom door was unsightly dirty"

Reviewed on Jun 3, 2026

Holiday Inn Youngstown South by IHG
Quality Inn & Suites New Castle

Quality Inn & Suites New Castle

2.5 out of 5
1740 New Butler Rd New Castle PA
Fully refundable
$87 nightly
The price is $97 total per night from Jul 5 to Jul 6
$97 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (951 reviews)
"The hotel staff are really nice and helpful. My room was clean and comfortable. Just be aware that there is no elevator in this hotel. Even half of the downstairs rooms have a small flight of stairs you need to go up. If you have mobility issues, this might be a challenge. I had torn my meniscus ..."

Reviewed on Jun 5, 2026

Quality Inn & Suites New Castle
DoubleTree by Hilton Youngstown Downtown

DoubleTree by Hilton Youngstown Downtown

4 out of 5
44 E Federal St Youngstown OH
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $135 total per night from Jun 21 to Jun 22
$135 total
Jun 21 - Jun 22
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
"Very nice hotel!"

Reviewed on Jun 2, 2026

DoubleTree by Hilton Youngstown Downtown
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.

Find the Best Oakland Vacation Packages

Oakland Essential Information

Language
English
Currency
U.S dollars
Population
1,550
Top Sights
McConnells Mill State Park, Living Treasures Wild Animal Park and Harlansburg Station

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Frequently asked questions

How much does an Oakland vacation package cost?
Offering great value package deals from $420 on Expedia, you'll be pleasantly surprised at how much a vacation to Oakland costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Oakland?
If you're looking to snag a cheap Oakland vacation package, consider traveling in November, December and January. You're likely to find lower prices on hotels and airfares during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Oakland?
The ideal duration for your Oakland vacation depends on what you'd like to see and do. Usually, a few days to a week will give you time to tick off all the main sights and explore some hidden treasures along the way.
How to find the best Oakland package deals?
Use Expedia's handy filters to find some of the best Oakland package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Oakland package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking stays and flights separately. Better still, you can customize your Oakland trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Oakland?
Land incredible discounts by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Oakland break.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Oakland trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.