Oakland Holidays

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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
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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 Benedum Center or Heinz Hall might round out your trip, and you can jump aboard the metro at Wood Street Station or Steel Plaza Station to get around town.

Find hotels in Downtown Pittsburgh

Our pick of the best 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
Fully refundableReserve now, pay when you stay
The price is NZ$238 per night from 29 Dec to 30 Dec
NZ$238
29 Dec - 30 Dec
includes taxes & fees
8.8/10 Excellent! (558 reviews)
Nice hotel in many ways. Liked the room, the fitness center, the staff and the location. Only concern was noise in the wee hours from a neighboring construction site and loudly closing room doors (a problem that could easily be resolved with dampening).

Reviewed on 24 Dec 2025

Courtyard by Marriott Pittsburgh University Center
The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is NZ$408 per night from 29 Dec to 30 Dec
NZ$408
29 Dec - 30 Dec
includes taxes & fees
9.2/10 Wonderful! (729 reviews)
Great staff, beautiful room and we loved the restaurant!

Reviewed on 24 Dec 2025

The Oaklander Hotel, Autograph Collection
Hampton Inn Pittsburgh University/Medical Center

Hampton Inn Pittsburgh University/Medical Center

2.5 out of 5
3315 Hamlet Street Pittsburgh PA
8/10 Very Good! (1,000 reviews)
Easy access to highways in and out of Pittsburgh

Reviewed on 22 Sept 2025

Get rates
Hampton Inn Pittsburgh University/Medical Center
See all 1,858 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 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.

Discover the most popular places to visit in Oakland

University of Pittsburgh

University of Pittsburgh

Explore the campus of University of Pittsburgh, a top university in Pittsburgh. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

University of Pittsburgh
Carnegie Museum of Natural History featuring views and interior views

Carnegie Museum of Natural History

Animal, vegetable, mineral – this museum has it all, with interactive displays to delight visitors of all ages.

Carnegie Museum of Natural History
Cathedral of Learning showing a church or cathedral, heritage elements and interior views

Cathedral of Learning

Take an audio tour and admire the majestic Commons Room and Nationality Rooms in one of the world’s tallest Gothic buildings.

Cathedral of Learning

Activities

Looking up to find cool details in the Downtown Skyline

Best of the Burgh Walking Tour of Pittsburgh

NZ$51
per adult
100% of travellers recommend
Best of the Burgh Walking Tour of Pittsburgh
Make new friends as you learn the exciting history of whiskey in Pittsburgh

Whiskey Rebellion & Prohibition Tour

NZ$78
per adult
Whiskey Rebellion & Prohibition Tour
City Brew Tours

Pittsburgh Signature Guided Brewery Tour

NZ$181
per adult
Pittsburgh Signature Guided Brewery Tour
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.