Oakland Vacations from $526

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The Latest Oakland vacation packages

Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $721, price is now $526 per person
$526
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
8/10 Very Good! (310 reviews)
Great job

Reviewed on Jul 26, 2026

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,100, price is now $738 per person
$738
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (3,662 reviews)
Hotel was very clean and in a wonderful area of the city. Close to restaurants and attractions.

Reviewed on Jul 30, 2026

Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside

3 out of 5
Bloomfield
Price was $739, price is now $549 per person
$549
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
9/10 Wonderful! (1,005 reviews)

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $1,054, price is now $836 per person
$836
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,583 reviews)

Crowne Plaza Suites Pittsburgh South by IHG

Crowne Plaza Suites Pittsburgh South by IHG

3.5 out of 5
Price was $813, price is now $657 per person
$657
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)

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Oakland Hotel Deals

Wingate by Wyndham Grove City

Wingate by Wyndham Grove City

3 out of 5
118 Garrett Dr Grove City PA
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $105 total per night from Aug 30 to Aug 31
$105 total
Aug 30 - Aug 31
Total with taxes and fees
Wingate by Wyndham Grove City
Microtel Inn & Suites By Wyndham Beaver Falls

Microtel Inn & Suites By Wyndham Beaver Falls

2.5 out of 5
2801 Darlington Rd Beaver Falls PA
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $86 total per night from Aug 2 to Aug 3
$86 total
Aug 2 - Aug 3
Total with taxes and fees
Microtel Inn & Suites By Wyndham Beaver Falls
Comfort Suites Youngstown North

Comfort Suites Youngstown North

2.5 out of 5
201 Perni Ln Youngstown OH
Fully refundable
$105 nightly
The price is $121 total per night from Aug 23 to Aug 24
$121 total
Aug 23 - Aug 24
Total with taxes and fees
Comfort Suites Youngstown North
See all 253 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 $526 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.