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South Side Vacations

Pack those stellar shades. We have South Side 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 South Side – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with South Side 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 South Side

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 South Side 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 South Side well.

Top Hotel Deals

See all 213 Properties in South Side
HYATT house Pittsburgh-South Side

HYATT house Pittsburgh-South Side

2795 S Water St, Pittsburgh
    3.0 out of 5.0
     
     

    Located in South Side Flats, this hotel is 1.1 mi (1.8 km) from Rex Theater and within 3 mi (5 km) of University of Pittsburgh and Carnegie Mellon University. ...

    HYATT house Pittsburgh-South Side$142

    HYATT house Pittsburgh-South Side$142
    Holiday Inn Express Hotel & Suites Pittsburgh-South Side

    Holiday Inn Express Hotel & Suites Pittsburgh-South Side

    20 S 10th St, Pittsburgh
      3.0 out of 5.0
       
       

      Located in South Side Flats, this hotel is within 1 mi (2 km) of Rex Theater and Monongahela Incline. University of Pittsburgh and PNC Park are also within 3 ...

      Holiday Inn Express Hotel & Suites Pittsburgh-South Side$93

      Holiday Inn Express Hotel & Suites Pittsburgh-South Side$93
      Morning Glory Inn

      Morning Glory Inn

      2119 Sarah Street, Pittsburgh
        3.5 out of 5.0
         
         

        Located in South Side Flats, this bed & breakfast is 0.4 mi (0.7 km) from Rex Theater and within 3 mi (5 km) of University of Pittsburgh and Monongahela Incline. ...

        Morning Glory Inn$150

        Morning Glory Inn$150
        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
          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 ...

            Drury Plaza Hotel Pittsburgh Downtown$150

            Drury Plaza Hotel Pittsburgh Downtown$150
            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$99

              Wyndham Grand Pittsburgh Downtown$99
              Distrikt Hotel Pittsburgh

              Distrikt Hotel Pittsburgh

              453 Boulevard of the Allies, Pittsburgh
                3.5 out of 5.0
                 
                 

                Located in Downtown Pittsburgh, this hotel is within a 15-minute walk of Allegheny County Courthouse and Monongahela Incline. PNC Park and Heinz Field are also ...

                Distrikt Hotel Pittsburgh$139

                Distrikt Hotel Pittsburgh$139
                Hyatt Regency Pittsburgh International Airport

                Hyatt Regency Pittsburgh International Airport

                1111 Airport Blvd, Pittsburgh
                  3.5 out of 5.0
                   
                   

                  An enclosed, climate-controlled, moving walkway connects this well-appointed hotel directly to Pittsburgh International Airport. IKEA and other top shopping ...

                  Hyatt Regency Pittsburgh International Airport$132

                  Hyatt Regency Pittsburgh International Airport$132
                  La Quinta Inn Pittsburgh Airport

                  La Quinta Inn Pittsburgh Airport

                  8507 University Blvd, Coraopolis
                    2.5 out of 5.0
                     
                     

                    This family-friendly Coraopolis hotel is located near the airport, within 2 mi (3 km) of Joe Walton Football Stadium and Robert Morris University. Moon Park ...

                    La Quinta Inn Pittsburgh Airport$72

                    La Quinta Inn Pittsburgh Airport$72
                    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

                      Top Flight Deals

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