Oakland Vacations from $404

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The Latest Oakland vacation packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was $512, price is now $404 per person
$404
per person
May 8 - May 10
found 11 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (3,437 reviews)
Yes breakfast was amazing

Reviewed on Mar 30, 2026

Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
Price was $816, price is now $622 per person
$622
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,607 reviews)
Large 1 bedroom suites. Helpful staff. Very centrally located

Reviewed on Mar 29, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $686, price is now $528 per person
$528
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (71 reviews)
Amazing kitchen,trash chute is fantastic. The staff were the best Room was so clean. Proximity to everything is perfect.

Reviewed on Mar 30, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $655, price is now $509 per person
$509
per person
May 8 - May 10
found 11 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.

Reviewed on Jan 10, 2026

TownePlace Suites by Marriott Pittsburgh Cranberry Township

TownePlace Suites by Marriott Pittsburgh Cranberry Township

3 out of 5
Price was $529, price is now $416 per person
$416
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
9.2/10 Wonderful! (429 reviews)
Nice hotel & room. Good breakfast. Great location, although a little difficult to find initially. Would recommend.

Reviewed on Mar 22, 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
$82 nightly
The price is $95 total per night from Apr 5 to Apr 6
$95 total
Apr 5 - Apr 6
Total with taxes and fees
8.6/10 Excellent! (706 reviews)
Nice hotel. Expedia messed up the booking the first night I was supposed to stay there, but the staff was great in helping me get a refund and suggesting other places to stay when they didn't have any more rooms.

Reviewed on Mar 25, 2026

Holiday Inn Youngstown South by IHG
Wingate by Wyndham Grove City

Wingate by Wyndham Grove City

2.5 out of 5
118 Garrett Dr Grove City PA
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $102 total per night from Apr 5 to Apr 6
$102 total
Apr 5 - Apr 6
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Great room, very friendly staff, breakfast and snack options were on par, great location as well.

Reviewed on Mar 29, 2026

Wingate by Wyndham Grove City
SureStay by Best Western Grove City

SureStay by Best Western Grove City

2.5 out of 5
1924 Leesburg Grove City Road Grove City PA
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $77 total per night from Apr 7 to Apr 8
$77 total
Apr 7 - Apr 8
Total with taxes and fees
7.2/10 Good! (1,002 reviews)
The staff was excellent! This is an older property but it was clean. Breakfast was eh. Very limited selection. The indoor pool was very well maintained. I would stay here again

Reviewed on Mar 30, 2026

SureStay by Best Western Grove City
See all 242 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 $404 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.