The Mellon Institute at Carnegie Mellon University with classical columns and a Gothic cathedral in the background.

Oakland Vacations from $532

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Your Oakland Vacation

From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. 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 vacation is simple with Expedia.

The Latest Oakland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A reception area with a tiled floor, two patterned armchairs, a desk with a reception sign, and a large mirror.
    Jan 15 - Jan 18

    Americas Best Value Inn Pittsburgh Airport + Flight

    Coraopolis
    3 nights
    2.0 star property
    6.6/10 - (1,002 reviews)
    "The room was ok clean. The top cover of the bed looked very dirty. The water pressure was very low and the heater wasn’t working well. But for the rate it was ok for a 12 hour stay."
    Reviewed November 10, 2026
    Roundtrip • Los Angeles (LAX) - Pittsburgh (PIT)
    LAX - PIT • Nonstop PIT - LAX • Nonstop
    $626
    $532
    per traveler
    found 1 day ago
    Americas Best Value Inn Pittsburgh Airport
  • A brick building with a large arched entrance labeled "STAYPGH".
    Jan 15 - Jan 18

    Stay Pittsburgh + Flight

    Downtown Pittsburgh
    3 nights
    2.0 star property
    8.0/10 - Very good (346 reviews)
    Roundtrip • Los Angeles (LAX) - Pittsburgh (PIT)
    LAX - PIT • Nonstop PIT - LAX • Nonstop
    $777
    $637
    per traveler
    found 1 day ago
    Stay Pittsburgh
  • A modern hotel room with a large window, a sofa, and a dining area.
    Jan 15 - Jan 18

    Fairmont Pittsburgh + Flight

    Downtown Pittsburgh
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,004 reviews)
    "Garage parking was super convenient and easy, rooms were clean and very comfortable."
    Reviewed November 8, 2026
    Roundtrip • Los Angeles (LAX) - Pittsburgh (PIT)
    LAX - PIT • Nonstop PIT - LAX • Nonstop
    $893
    $747
    per traveler
    found 1 day ago
    Fairmont Pittsburgh
  • An indoor swimming pool with a diving area, surrounded by seating and a bar area.
    Jan 15 - Jan 18

    DoubleTree by Hilton Pittsburgh - Green Tree + Flight

    Pittsburgh
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,305 reviews)
    Roundtrip • Los Angeles (LAX) - Pittsburgh (PIT)
    LAX - PIT • Nonstop PIT - LAX • Nonstop
    $770
    $651
    per traveler
    found 1 day ago
    DoubleTree by Hilton Pittsburgh - Green Tree
  • The entrance of the Hotel Monaco with a grand facade, a receptionist at the entrance, and a statue of a dog on the right.
    Jan 15 - Jan 18

    Kimpton Hotel Monaco Pittsburgh by IHG + Flight

    Downtown Pittsburgh
    3 nights
    4.5 star property
    9.4/10 - Exceptional (1,320 reviews)
    "Loved the on-site restaurant, The Commoner, for dinner - delicious steak and dessert - and ability to order in-room service, as well. Breakfast was one of the best we’ve ever had (avocado toast, bacon, breakfast sandwiches, fresh juices). Beautiful room/loved the bed/bathroom was perfect."
    Reviewed November 10, 2026
    Roundtrip • Los Angeles (LAX) - Pittsburgh (PIT)
    LAX - PIT • Nonstop PIT - LAX • Nonstop
    $954
    $818
    per traveler
    found 1 day ago
    Kimpton Hotel Monaco Pittsburgh by IHG

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Learn more about Oakland
A yellow bridge over a river with a cityscape in the background.

Downtown Pittsburgh

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.

A city skyline at dusk with illuminated buildings, a prominent bridge, and a river.
Photo by TM
Open Photo by TM

North Shore

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.

A building with a large sign reading 'THE TERMINAL' and storefronts for 'posman books' and 'solidcore.'
Photo by TM
Open Photo by TM

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.

A bridge with illuminated lights reflecting on the water, a city skyline in the background, and a smokestack emitting smoke.

North Side

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.

A greenhouse with geometrically shaped flower beds and statues.

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.

Discover the most popular places to visit in Oakland

A museum with dinosaur exhibits and a large tree sculpture.

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.
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What to do near Oakland

Picture 3 for Activity Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

$29
per adult
86% of travelers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
See all activities near Oakland

Oakland Hotel Deals

A Courtyard by Marriott hotel with a modern design, featuring a prominent entrance, flag display, and landscaped surroundings.

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center
3.5 star property
Oakland
9.0 out of 10, Wonderful, (982 reviews)
"Everything was great except one item.. Make sure to specifically ask about parking cost. The way it was presented to me was that parking was included but it was not. I specifically asked if there was a cost and I was told no but there was. Other than that everything was great!"
$104 nightly
The price is $119
Nov 23 - Nov 24
Total with taxes and fees
Courtyard by Marriott Pittsburgh University Center
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.
See all properties in Oakland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.