Oakland Holidays
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Your Oakland Holiday
From its cycling to its walking, there's tons to love about Oakland. Book a customised Oakland holiday package and get ready to fall for the delights of this neighbourhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland holiday is simple with Expedia.
Our guide on where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
Abundant dining options, interesting museums and live music are just a few top things to explore in Downtown Pittsburgh. A visit to PPG Paints Arena or Benedum Center might round out your trip, and you can jump aboard the metro at Wood Street Station or Steel Plaza Station to get around town.
North Shore
2 out of top 10 points of interest in this area
Visitors often come to North Shore for its stunning river views, but many stay to explore sights like PNC Park and Acrisure Stadium. Getting around the area on the metro is easy if you take a ride at North Side Station.
Strip District
Strip District is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to The Terminal or Senator John Heinz Regional History Centre.
North Side
1 out of top 10 points of interest in this area
While you're in North Side, take in top sights like PNC Park or Acrisure Stadium, and hop on the metro to see more of the city at North Side Station or Allegheny Station.
Shadyside
Unique features of Shadyside include the restaurants and shopping. Make a stop by Walnut Street or Gallerie CHIZ while you're exploring the area.
Our pick of the best Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
AU$226
4 Nov - 5 Nov
includes taxes & fees
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
AU$193
8 Nov - 9 Nov
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Close to medical facilities at UPMC, this hotel was perfect for us. Zoe was so helpful and welcoming upon check-in. It's a newer building and everything was clean and well-lighted. Our room was more like a suite with two televisions, separate couch and seating area for one of them. Bed was comfortable ..."
Reviewed on 14 Oct 2026
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
AU$354
4 Nov - 5 Nov
includes taxes & fees
9.2/10 Wonderful! (846 reviews)
"Great location, upscale amenities and really tasty food."
Reviewed on 12 Oct 2026
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 holiday package cost?
Starting from as low as , a holiday 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 Centre. 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 holiday?
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 holiday package?
With a holiday 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 holiday package?
Your situation can change in a flash, so yes, you can. You may be able to cancel and rebook your Oakland holiday 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.
Stay near popular Oakland attractions
Carnegie Museum of Natural History
9.2/10 (58 reviews)
Natural wonders from across the world are showcased in this marvellous museum. Discover deadly dinosaurs and glistening gems, or go on a safari through the Savannah.
Carnegie Museum of Art
9.8/10 (7 reviews)
Founded in 1896 by steel baron Andrew Carnegie, this contemporary art institution boasts an impressive fusion of painting, sculpture, architecture and furniture.
Heinz Memorial Chapel
Hosting about 1,000 events per year, this non-sectarian chapel welcomes all and frequently hosts weddings, lectures and concerts as well as religious services.
Soldiers and Sailors Memorial Hall and Museum
10.0/10 (1 review)
You can spend an afternoon browsing the exhibits at Soldiers and Sailors Memorial Hall and Museum in Pittsburgh. Attend a sporting event or visit the shops in this family-friendly area.
Cathedral of Learning
9.6/10 (184 reviews)
Take an audio tour and admire the majestic Commons Room and Nationality Rooms in one of the world’s tallest Gothic buildings.
Petersen Events Center
10.0/10 (3 reviews)
Catch an event at Petersen Events Center during your trip to Pittsburgh. Amble around this vibrant area's riverfront or attend a sporting event.
Carnegie Library of Pittsburgh
8.6/10 (7 reviews)
Carnegie Library of Pittsburgh is just one of the places to see in Pittsburgh, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Pittsburgh Playhouse
You can get tickets for a performance at Pittsburgh Playhouse during your stay in Pittsburgh. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.
Activities
Pittsburgh: Museum of Illusions Entrance Ticket
AU$41
per adult
86% of travellers recommend
Best of the Burgh Walking Tour of Pittsburgh
AU$46
per adult
100% of travellers recommend
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
AU$18
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.