Oakland Vacations from ￥256,994

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, 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.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was ￥309,406, price is now ￥256,994 per person
￥256,994
per person
Jun 15 - Jun 19
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
8.2/10 Very Good! (3,476 reviews)
Room was clean and comfortable, plenty of food options nearby.

Reviewed on Apr 26, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was ￥378,768, price is now ￥328,725 per person
￥328,725
per person
Jun 15 - Jun 19
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,002 reviews)
It’s a nice hotel with friendly staff. I think you should give a discount or free parking for people staying at the hotel. The cost to parks adds up quick.

Reviewed on Apr 10, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was ￥316,798, price is now ￥286,695 per person
￥286,695
per person
Jun 15 - Jun 19
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
8.4/10 Very Good! (92 reviews)
Pros: cRoom was clean and nice size. Kitchen had everything we have it at home except for food. Bed was very comfortable. Staff and valet were very helpful. We arrived to town early and were checked in at 1pm which was nice, because we wanted to walk to the NFL draft. Cons: one side of the hotel is next to train tracks, Friday night we counted four trains and could hear the trains loud and clear. We counted 4 trains pass by our room between 11 PM and 3:30 AM, so we didn’t sleep most of the night. The hotel has virtually no amenities, no restaurant, and no free breakfast.

Reviewed on Apr 26, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was ￥291,190, price is now ￥263,563 per person
￥263,563
per person
Jun 15 - Jun 19
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
8.4/10 Very Good! (1,476 reviews)
Ive never stayed at a hotel with valet parking before. Parking situations tend to make me anxious and I had no idea what to expect. We pulled up and a guy came right over and talked to us. Asked how long we'd be staying, how soon we would need the car if at all during the stay and all that. Check in was fairly normal as any other place. Fast and easy. We stayed for St. Pats and one of the biggest things we were excited about was utilizing the rooftop to watch the parade and what an amazing experience that was!! Highly recommend! The only thing that I think could've been better (which is really just my own opinion) is better explaining the hold that is placed on your card when you check in, then how the valet parking is deducted from that hold rather than you paying. It was a little confusing when i saw it all on my statement but i did work everything out and it was fine! Definitely plan to come back for another stay

Reviewed on Apr 28, 2026

Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
Price was ￥302,440, price is now ￥279,168 per person
￥279,168
per person
Jun 15 - Jun 19
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,668 reviews)
Loved Etage location. Walked to a pirates game one night then walked to a Penguins game the next day. Walked to meet my child at Duquesne University.

Reviewed on Apr 26, 2026

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh

Downtown Pittsburgh

2 out of top 10 points of interest in this area
4.5/5(2,278 area reviews)

Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.

Find hotels in Downtown Pittsburgh

Oakland Hotel Deals

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue Pittsburgh PA
The price is ￥21,544 per night from May 25 to May 26
￥21,544
￥24,560 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (698 reviews)
Very nice room Comfortable bed

Reviewed on Apr 28, 2026

Courtyard by Marriott Pittsburgh University Center
Residence Inn Pittsburgh Oakland/University Place

Residence Inn Pittsburgh Oakland/University Place

3 out of 5
3341 Forbes Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is ￥20,245 per night from May 25 to May 26
￥20,245
￥23,079 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (971 reviews)
The hotel was very clean, and the staff was so courteous.

Reviewed on Apr 27, 2026

Residence Inn Pittsburgh Oakland/University Place
Hotel Indigo Pittsburgh University-Oakland by IHG

Hotel Indigo Pittsburgh University-Oakland by IHG

3.5 out of 5
329 Technology Drive Pittsburgh PA
Fully refundable
The price is ￥18,810 per night from May 25 to May 26
￥18,810
￥21,443 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Room was very clean and staff were nice

Reviewed on Apr 28, 2026

Hotel Indigo Pittsburgh University-Oakland by IHG
See all 2,066 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.

Frequently asked questions

How much does an Oakland vacation package cost?
Starting from as low as ￥256,994, a vacation package is your passport to cheaper travel. Custom make your Oakland getaway by selecting from our great range of airfares, hotels and rental cars.
How do I get a cheap travel package to Oakland?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Hotels, rental cars, flights and activities — we've got everything you need. Choose the combination that suits you and watch your savings stack up. Of course, a package deal is never one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 properties throughout the world, which lets you customize your Oakland getaway.
Where should I stay in Oakland?
Visitors come from far and wide to see Acrisure Stadium and PNC Park in Oakland. Stay close to these awesome attractions and visit them at your leisure.
What are the top hotels in Oakland?
Get your trip off to an excellent start by booking a stay at Industrial Loft 3 Min To Hillman Cancer Center. It's one of most sought-after hotels in Oakland. Another option is New Huge Spacious 3 Bedroom In Oakland That Over 3000+ Sq Ft.
How far in advance should I book my Oakland vacation?
To bag rock-bottom prices, book ASAP. Airlines usually advertise flight tickets, along with some of the lowest fares, nearly 12 months prior to departure. Hotels, car rental and activities should also be booked early so you can have the pick of the bunch. If you were hoping for a last-minute getaway in Oakland, there are always plenty of great bargains to be had on Expedia. Book your escape today!
What does an Expedia Oakland travel package include?
It all depends on what sort of trip you have in the works. Oakland travel deals can include car rentals, hotels and flights. You can mix and match to find the package that works for you! You can also add on activities and experiences after you've booked to pick up even bigger discounts.
What should I know before booking an Oakland travel package?
An Expedia travel package can be customized for your circumstances and is a great way to stretch your hard-earned dollars. What you include is totally up to you. Rental cars, hotels and flights — decide on a combination that suits your plans.
Can I choose my airline with an Oakland Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you want to fly to Oakland in coach or first class, simply select from the available airline options. Expedia has access to more than 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Oakland vacation package?
Your situation can change in a flash, so yes, you can. You may be able to cancel and rebook your Oakland vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel or make changes, but your airline, hotel or car rental company may impose a fee. Looking for more information? Visit our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Oakland

University of Pittsburgh in Pittsburgh, PA

University of Pittsburgh

4.5/5(856 reviews)

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

University of Pittsburgh
Carnegie Museum of Natural History

Carnegie Museum of Natural History

4.5/5(50 reviews)

From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.

Carnegie Museum of Natural History
Allegheny County Soldiers memorial; Shutterstock ID 10100599

Soldiers and Sailors Memorial Hall and Museum

You can spend an afternoon browsing the exhibits at Soldiers and Sailors Memorial Hall and Museum during your trip to Pittsburgh. Attend a sporting event or visit the shops in this vibrant area.

Soldiers and Sailors Memorial Hall and Museum

Things to do

Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

￥11,005
per adult
Pittsburgh Pirates Baseball Game at PNC Park
Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

￥4,606
per adult
80% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
Pittsburgh Pirates Home Game Ticket at PNC Park

Pittsburgh Pirates Home Game Ticket at PNC Park

￥3,809
per adult
Pittsburgh Pirates Home Game Ticket at PNC Park
See all activities in Pittsburgh
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.