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South Boston Vacations

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

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

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 Boston 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 Boston well.

South Boston Flight + Hotel packages

Top Hotel Deals

See all 1,225 Hotels in South Boston
Aloft Boston Seaport District

Aloft Boston Seaport District

401-403 D Street, Boston
    3.0 out of 5.0
     
     

    Located in Innovation District, this hotel is within a 15-minute walk of Boston Convention and Exhibition Center, World Trade Center, and Institute of Contemporary ...

    Aloft Boston Seaport District$142

    Aloft Boston Seaport District$142
    Seaport Boston Hotel

    Seaport Boston Hotel

    1 Seaport Lane, Boston
      4.0 out of 5.0
       
       

      Atop Commonwealth Pier, near the Seaport World Trade Center and the Boston Convention & Exhibit Center, this hotel is one mile from the Financial District, three ...

      Seaport Boston Hotel$206

      Seaport Boston Hotel$206
      YOTEL Boston

      YOTEL Boston

      65 Seaport Blvd, Boston
        3.5 out of 5.0
         
         

        Located in the city center of Boston, this hotel is near the airport and within walking distance of Institute of Contemporary Art, Boston Children's Museum, ...

        Element Boston Seaport District

        Element Boston Seaport District

        391-395 D Street, Boston
          3.0 out of 5.0
           
           

          Located in Innovation District, this hotel is within a 15-minute walk of Boston Convention and Exhibition Center and World Trade Center. Institute of Contemporary ...

          Element Boston Seaport District$157

          Element Boston Seaport District$157
          The Westin Boston Waterfront

          The Westin Boston Waterfront

          425 Summer St, Boston
            4.0 out of 5.0
             
             

            Located in Seaport, The Westin Boston Waterfront is connected to the Boston Convention & Exhibition Center, a 7-minute drive from Logan International Airport. ...

            The Westin Boston Waterfront$163

            The Westin Boston Waterfront$163
            Renaissance Boston Waterfront Hotel

            Renaissance Boston Waterfront Hotel

            606 Congress St, Boston
              4.0 out of 5.0
               
               

              Just south of the downtown core, this Seaport District hotel overlooks Boston Harbor and is 0.3 mile from the Boston Convention & Exhibition Center. Faneuil ...

              Renaissance Boston Waterfront Hotel$207

              Renaissance Boston Waterfront Hotel$207
              The Envoy Hotel, Autograph Collection

              The Envoy Hotel, Autograph Collection

              70 Sleeper Street, Boston
                4.0 out of 5.0
                 
                 

                Located in Innovation District, this hotel is within a 10-minute walk of Boston Children's Museum, Boston Tea Party Ship, and Institute of Contemporary Art. ...

                The Envoy Hotel, Autograph Collection$239

                The Envoy Hotel, Autograph Collection$239
                Residence Inn by Marriott Boston Downtown/Seaport

                Residence Inn by Marriott Boston Downtown/Seaport

                370 Congress St, Boston
                  3.0 out of 5.0
                   
                   

                  Located in Innovation District, this hotel is within a 5-minute walk of Boston Children's Museum and Boston Tea Party Ship. Boston Convention and Exhibition ...

                  Residence Inn by Marriott Boston Downtown/Seaport$199

                  Residence Inn by Marriott Boston Downtown/Seaport$199
                  Global Luxury Suites at South Boston

                  Global Luxury Suites at South Boston

                  730 E Broadway, Boston
                    4.0 out of 5.0
                     
                     

                    This apartment building is located in Boston (South Boston), close to Black Falcon Cruise Terminal, Boston Convention and Exhibition Center, and World Trade ...

                    Seaport Signal Building by Vacasa

                    Seaport Signal Building by Vacasa

                    154 West 2nd Street, Boston
                      4.0 out of 5.0
                       
                       

                      Located in South Boston, this apartment building is within 1 mi (2 km) of Tufts University, Boston Convention and Exhibition Center, and Boston Children's Museum. ...

                      Top Flight Deals

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