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

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $552, price is now $420 per person
$420
per person
Jul 6 - Jul 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.4/10 Very Good! (1,518 reviews)
I havnt slept that good in a while , right when I woke up I lifted the sheets to see what brand mattress and pillows they were. 100 out of 10

Reviewed on Jun 5, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $721, price is now $513 per person
$513
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8/10 Very Good! (287 reviews)
The unit was more thsn adequate, clean, well equipped, and quiet. Great place and great value.

Reviewed on Jun 4, 2026

The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
Oakland
Save 100% on your flight
Price was $1,278, price is now $1,024 per person
$1,024
per person
Jul 28 - Aug 3
found 11 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
9.2/10 Wonderful! (780 reviews)
Great!!! John, the concierge was incredible!!! Thanks

Reviewed on Jun 1, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $570, price is now $458 per person
$458
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.6/10 Excellent! (112 reviews)
good location, perfect for family travel

Reviewed on Jun 3, 2026

Traveler's Rest Hotel

Traveler's Rest Hotel

2 out of 5
South Side Flats
Price was $941, price is now $759 per person
$759
per person
Jul 28 - Aug 3
found 11 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
9.6/10 Exceptional! (100 reviews)
Perfect stay! The attention to detail, full fridge , friendly host , great room. This made our stay in Pittsburgh a special one . Thank you !

Reviewed on May 27, 2026

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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
See all 248 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.

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.