Oakland Vacation Packages
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Top Holiday Package Deals in Oakland
Price found within the past 48 hours. Click for updated prices.
The Inn on Negley
Shadyside
CA $1,285
per person
Nov 13 - Nov 16
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
10/10 Exceptional! (225 reviews)
This Inn is beautiful, perfectly located within a couple minutes of downtown, very well maintained, breakfast was wonderful, the room was super comfortable with quality linens and a very comfortable batch. Wonderful staff as well, Peter gave us some history of Pittsburgh and some ideas to make our trip back home even better! We plan on coming back to Pittsburgh and staying here again.
Reviewed on Sep 30, 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
2 out of top 10 points of interest in this area
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.
North Shore
2 out of top 10 points of interest in this area
Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations.
Strip District
Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months.
Shadyside
Victorian mansions and modern apartments create a diverse residential atmosphere. Explore upscale stores on Walnut Street, dine at local eateries like Pamela's Diner, and easily walk between the three business corridors. Public transportation is accessible.
North Side
1 out of top 10 points of interest in this area
If you're spending time in North Side, check out sights like PNC Park or Acrisure Stadium and hop on the metro to see more the city at North Side Station or Allegheny Station.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $186
CA $212 total
Nov 2 - Nov 3
includes taxes & fees
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
CA $172
CA $196 total
Nov 2 - Nov 3
includes taxes & fees
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $176
CA $201 total
Oct 22 - Oct 23
includes taxes & fees
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 CA $947, 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.
Stay near popular Oakland attractions
Carnegie Museum of Natural History
9.2/10 (58 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 Art
9.8/10 (7 reviews)
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
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.
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.
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 during your trip to Pittsburgh. Attend a sporting event or visit the shops in this family-friendly area.
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 make plans for a show at Pittsburgh Playhouse during your trip to Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Things to do
Pittsburgh: Museum of Illusions Entrance Ticket
CA $41
per adult
86% of travellers recommend
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
CA $18
per adult
Pittsburgh Steelers Football Game at Acrisure Stadium
CA $428
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.