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Shadyside Vacations

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

Hotwire can help you find your travel bliss with Shadyside 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 Shadyside

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 Shadyside 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 Shadyside well.

Top Hotel Deals

See all 205 Hotels in Shadyside
Mansions on Fifth Hotel

Mansions on Fifth Hotel

5105 Fifth Avenue, Pittsburgh
    4.0 out of 5.0
     
     

    Located in Shadyside, this romantic hotel is within 1 mi (2 km) of Heinz Memorial Chapel, University of Pittsburgh, and Carnegie Mellon University. Carnegie ...

    The Inn on Negley

    The Inn on Negley

    703 South Negley Ave., Pittsburgh
      4.0 out of 5.0
       
       

      Located in Shadyside, this bed & breakfast is within 2 mi (3 km) of UPMC Shadyside, University of Pittsburgh, and Carnegie Mellon University. Chatham University ...

      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$119

          Distrikt Hotel Pittsburgh$119
          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
              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$131

                Hyatt Regency Pittsburgh International Airport$131
                La Quinta Inn Pittsburgh Airport

                La Quinta Inn Pittsburgh Airport

                8507 University Blvd, Coraopolis
                  2.5 out of 5.0
                   
                   

                  Situated near the airport, this hotel is 1 mi (1.6 km) from Joe Walton Football Stadium and 1.3 mi (2.2 km) from Robert Morris University. Moon Golf Club and ...

                  La Quinta Inn Pittsburgh Airport$76

                  La Quinta Inn Pittsburgh Airport$76
                  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$125

                    Wyndham Pittsburgh University Center$125
                    Sheraton Pittsburgh Hotel at Station Square

                    Sheraton Pittsburgh Hotel at Station Square

                    300 West Station Square Drive, Pittsburgh
                      3.5 out of 5.0
                       
                       

                      Standing along the banks of the Monongahela River, this hotel is in Station Square, the city's playground, brimming with restaurants, shops, and nightlife; the ...

                      Sheraton Pittsburgh Hotel at Station Square$130

                      Sheraton Pittsburgh Hotel at Station Square$130

                      Top Flight Deals

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