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Oakland Vacations

Pack those stellar shades. We have Oakland vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Oakland – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Oakland vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Oakland

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Oakland vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Oakland well.

Top Hotel Deals

See all 204 Hotels in Oakland
Wyndham Pittsburgh University Center

Wyndham Pittsburgh University Center

100 Lytton Avenue, Pittsburgh
    3.5 out of 5.0
     
     

    Located in Oakland, this hotel is within 1 mi (2 km) of Soldiers and Sailors Memorial Hall and Museum, University of Pittsburgh, and Carnegie Mellon University. ...

    Wyndham Pittsburgh University Center$118

    Wyndham Pittsburgh University Center$118
    Residence Inn Pittsburgh University/ Medical Center

    Residence Inn Pittsburgh University/ Medical Center

    3896 Bigelow Blvd, Pittsburgh
      3.0 out of 5.0
       
       

      Located in Oakland, this aparthotel is within a 15-minute walk of Heinz Memorial Chapel and University of Pittsburgh. Carnegie Mellon University is 1.2 mi (2 ...

      Residence Inn Pittsburgh University/ Medical Center$91

      Residence Inn Pittsburgh University/ Medical Center$91
      Quality Inn University Center

      Quality Inn University Center

      3401 Blvd Of The Allies, Pittsburgh
        2.5 out of 5.0
         
         

        Situated in Pittsburgh's Oakland, this hotel is 1 block from Magee-Women's Hospital. University of Pittsburgh Medical Center is a half-mile from the hotel and ...

        Quality Inn University Center$99

        Quality Inn University Center$99
        Residence Inn Pittsburgh Oakland/University Place

        Residence Inn Pittsburgh Oakland/University Place

        3341 Forbes Ave, Pittsburgh
          3.0 out of 5.0
           
           

          This hotel is located in Pittsburgh (Oakland), close to University of Pittsburgh Medical Center, Petersen Events Center, and Soldiers and Sailors Memorial Hall ...

          Residence Inn Pittsburgh Oakland/University Place$134

          Residence Inn Pittsburgh Oakland/University Place$134
          Hampton Inn Pittsburgh University/Medical Center

          Hampton Inn Pittsburgh University/Medical Center

          3315 Hamlet Street, Pittsburgh
            2.5 out of 5.0
             
             

            Located in Oakland, this hotel is within 1 mi (2 km) of Pittsburgh Playhouse and University of Pittsburgh. Carnegie Mellon University and Monongahela Incline ...

            Hampton Inn Pittsburgh University/Medical Center$107

            Hampton Inn Pittsburgh University/Medical Center$107
            Indigo Pittsburgh - Technology Center

            Indigo Pittsburgh - Technology Center

            329 Technology Drive, Pittsburgh
              3.5 out of 5.0
               
               

              This hotel is located in Pittsburgh (Oakland), close to Pittsburgh Playhouse, University of Pittsburgh, and Carnegie Mellon University. Also nearby are Phipps ...

              Indigo Pittsburgh - Technology Center$152

              Indigo Pittsburgh - Technology Center$152
              Omni William Penn Hotel

              Omni William Penn Hotel

              530 William Penn Place, Pittsburgh
                4.0 out of 5.0
                 
                 

                The historic Omni William Penn Hotel is opposite Steel Plaza T Station in downtown Pittsburgh. Guests can walk 4 blocks to Heinz Hall for the Performing Arts, ...

                Omni William Penn Hotel$139

                Omni William Penn Hotel$139
                Distrikt Hotel Pittsburgh

                Distrikt Hotel Pittsburgh

                453 Boulevard of the Allies, Pittsburgh
                  3.5 out of 5.0
                   
                   

                  This hotel is located in Pittsburgh (Downtown Pittsburgh), close to Allegheny County Courthouse, Monongahela Incline, and PNC Park. Also nearby are Duquesne ...

                  Distrikt Hotel Pittsburgh$89

                  Distrikt Hotel Pittsburgh$89
                  Drury Plaza Hotel Pittsburgh Downtown

                  Drury Plaza Hotel Pittsburgh Downtown

                  745 Grant Street, Pittsburgh
                    3.0 out of 5.0
                     
                     

                    Located in Downtown Pittsburgh, this hotel is within 1 mi (2 km) of U.S. Steel Tower, PNC Park, and Monongahela Incline. University of Pittsburgh and Heinz Field ...

                    Wyndham Grand Pittsburgh Downtown

                    Wyndham Grand Pittsburgh Downtown

                    600 Commonwealth Pl, Pittsburgh
                      3.5 out of 5.0
                       
                       

                      This downtown hotel is at the gateway to the cultural district, facing Point State Park and Pittsburgh's famed Three Rivers.

                      Wyndham Grand Pittsburgh Downtown$124

                      Wyndham Grand Pittsburgh Downtown$124

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.