Oakland Vacations from $625
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
The Latest Oakland vacation packages
Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh
Downtown Pittsburgh
$625
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Pittsburgh (PIT)
8/10 Very Good! (325 reviews)
Good location near a bunch of restaurants that you can walk to. We were in town for the Steelers game and this is a good place to stay for that. Easy to get an Uber/Lyft too if you need one. Apartment was very clean. Queen bed was good. Parking lot $30 per day across street. Would stay here again if in Downtown Pittsburgh area.
Reviewed on Sep 14, 2026
The Inn on Negley
Shadyside
$1,118
per person
Nov 7 - Nov 14
found 15 hours ago
Roundtrip flight included
Houston (HOU) to Pittsburgh (PIT)
10/10 Exceptional! (221 reviews)
This was the second time that I stayed at The Inn on Negley, and once again it was an incredible experience. The staff were warm and welcoming, with a special shout out to Eva. Her enthusiasm and hospitality was the highlight of our stay, and I can’t thank her enough for everything. We can’t wait to return!
Reviewed on Sep 15, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
$781
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Pittsburgh (PIT)
8.6/10 Excellent! (1,004 reviews)
I would highly recommend! We spent our 2nd anniversary there for the Steelers game and when we arrived to our room they were so kind to leave us some goodies and a little note to congratulate us! It was a very clean hotel and room! Staffing very kind! Will be staying again for sure!
Reviewed on Sep 14, 2026
461 Melwood Suites Unit 101 2Bed/2Bath
Oakland
$716
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Pittsburgh (PIT)
9.6/10 Exceptional! (4 reviews)
The bedrooms could use some furniture or shelves for clothing and some lamps or soft lights at night
Also no real table for a family meal
Great space, convenient and the parking is helpful and reasonably priced
Loved the bathrooms
Good place to stay
Reviewed on May 22, 2026
Oakland Hotel Deals
Holiday Inn Youngstown South by IHG
7410 South Ave Boardman OH
Fully refundable
$101 nightly
$117 total
Sep 20 - Sep 21
Total with taxes and fees
8.4/10 Very Good! (790 reviews)
"Great stay with friendly staff. The Dove personal care products were a really nice touch. The microfiber sheets were not nice. Please return to cotton. Met some family members at the bar one evening for drinks and the service was terrific."
Reviewed on Sep 14, 2026
Microtel Inn & Suites By Wyndham Beaver Falls
2801 Darlington Rd Beaver Falls PA
Fully refundableReserve now, pay when you stay
$76 nightly
$85 total
Sep 27 - Sep 28
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Everyone was extremely accommodating, thank you."
Reviewed on Sep 15, 2026
DoubleTree by Hilton Youngstown Downtown
44 E Federal St Youngstown OH
$121 nightly
$136 total
Oct 4 - Oct 5
Total with taxes and fees
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 |
More vacations you might like
Frequently asked questions
How much does an Oakland vacation package cost?
Offering great value package deals from $625 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.
