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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.

Top Hotel Deals

See all 32 Hotels in South Boston
Days Inn & Suites by Wyndham South Boston

Days Inn & Suites by Wyndham South Boston

1074 Bill Tuck Hwy, South Boston
    2.5 out of 5.0
     
     

    Situated in South Boston, this hotel is 3.5 mi (5.6 km) from South Boston Speedway and within 25 mi (40 km) of Hudson Heritage Farms and Mecklenburg County Veterans ...

    Days Inn & Suites by Wyndham South Boston$93

    Days Inn & Suites by Wyndham South Boston$93
    Fairfield Inn & Suites South Boston

    Fairfield Inn & Suites South Boston

    1120 Bill Tuck Hwy, South Boston
      2.5 out of 5.0
       
       

      Situated in South Boston, this hotel is 3.5 mi (5.6 km) from South Boston Speedway and within 20 mi (32 km) of Greenwood Vineyards and Staunton River State Park. ...

      Fairfield Inn & Suites South Boston$149

      Fairfield Inn & Suites South Boston$149
      The Berry Hill Resort & Conference Center

      The Berry Hill Resort & Conference Center

      3105 River Road, South Boston
        4.0 out of 5.0
         
         

        Situated in the historical district, this spa hotel is within 12 mi (20 km) of South Boston Speedway, Hudson Heritage Farms, and Greenwood Vineyards. Bright ...

        The Berry Hill Resort & Conference Center$137

        The Berry Hill Resort & Conference Center$137
        Super 8 by Wyndham South Boston VA

        Super 8 by Wyndham South Boston VA

        1040 Bill Tuck Hwy, South Boston
          2.0 out of 5.0
           
           

          Situated in South Boston, this motel is 3.5 mi (5.6 km) from South Boston Speedway and within 20 mi (32 km) of Greenwood Vineyards and Staunton River State Park. ...

          Super 8 by Wyndham South Boston VA$75

          Super 8 by Wyndham South Boston VA$75
          Quality Inn

          Quality Inn

          2001 Seymour Drive, South Boston
            2.5 out of 5.0
             
             

            Situated in South Boston, this hotel is 2.3 mi (3.7 km) from South Boston Speedway and within 20 mi (32 km) of Greenwood Vineyards and Staunton River State Park. ...

            Americas Best Value Inn & Suites - South Boston

            Americas Best Value Inn & Suites - South Boston

            2050 Philpott Rd, South Boston
              2.0 out of 5.0
               
               

              Located in the heart of South Boston, this motel is 5.8 mi (9.3 km) from South Boston Speedway and within 20 mi (32 km) of Hudson Heritage Farms and Greenwood ...

              Americas Best Value Inn & Suites - South Boston$54

              Americas Best Value Inn & Suites - South Boston$54
              Oak Grove Plantation

              Oak Grove Plantation

              1245 Cluster Springs Rd, South Boston
                3.0 out of 5.0
                 
                 

                Situated near the airport, in Cluster Springs, this bed & breakfast is in the same region as South Boston Speedway, Hudson Heritage Farms, and Roxboro Country ...

                Charles Bass House Bed & Breakfast

                Charles Bass House Bed & Breakfast

                1505 North Main Street, South Boston
                  2.5 out of 5.0
                   
                   

                  Situated in the historical district, this bed & breakfast is 2.5 mi (4 km) from South Boston Speedway and within 20 mi (32 km) of Greenwood Vineyards and Hudson ...

                  Charles Bass House Bed & Breakfast$115

                  Charles Bass House Bed & Breakfast$115
                  Astoria Hotel Danville West

                  Astoria Hotel Danville West

                  3020 Riverside Dr, Danville
                    2.0 out of 5.0
                     
                     

                    Situated near the airport, this motel is 0.9 mi (1.5 km) from Danville Mall and within 3 mi (5 km) of Ballou Park and Danvillian Gallery. The Historic North ...

                    Astoria Hotel Danville West$50

                    Astoria Hotel Danville West$50
                    Best Western Windsor Inn & Suites

                    Best Western Windsor Inn & Suites

                    1292 S Boston Rd, Danville
                      2.5 out of 5.0
                       
                       

                      Situated in Danville, this hotel is within 3 mi (5 km) of Legion Field, Anglers Park, and The Historic North Theatre. Danvillian Gallery is 3 mi (4.8 km) ...

                      Best Western Windsor Inn & Suites$72

                      Best Western Windsor Inn & Suites$72

                      Top Flight Deals

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