Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Start by selecting your hotel
Start by selecting your hotel
Start by selecting your hotel

Save up to $603 by booking Flight + Hotel.

Search 590,000 properties and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more


South Boston Vacation Travel Guide

Accommodation in South Boston

Using Expedia's hotel booking website is an easy way of securing a comfortable hotel in South Boston that matches your budget and taste.

The Fairfield Inn & Suites South Boston, at 1120 Bill Tuck Hwy, and the Days Inn & Suites South Boston, at 1074 Bill Tuck Hwy are two of the higher-quality accommodation options in South Boston. Stay at either and you'll be guaranteed to have some of the nicest guest services in town. More economical hotels worth considering are the Charles Bass House Bed & Breakfast, at 1505 North Main Street, and the Super 8 South Boston VA, at 1040 Bill Tuck Hwy.

It’s easy to book the getaway of your dreams when you search through our selection of South Boston vacations. Our goal? To create the perfect trip for you by providing the largest selection of vacation packages. Confidently book your getaway thanks to our trustworthy recommendations and verified consumer reviews from travelers just like you. Personalize your South Boston package with our myriad of hotel rooms and flight tickets, which help to create a vacation specifically for you. Simply sort through our selection and pick and choose the elements that best suit your preferences and price range.

Because we offer the best rates, you can book your travel reservations knowing you won’t find lower prices elsewhere. These discounts are so great, you’ll feel like you gained the title of the ultimate bargain hunter with our South Boston vacation package deals. Whether you’re looking to book multiple flights, stay at the fanciest hotel, or explore the hottest local attractions, you’ll find discounted travel arrangements within your budget right here. You shouldn’t have a care in the world when you go on vacation, so our discounts allow you to rest easy without giving your bank account a second thought. Save money on your vacation today and revel in your much-deserved getaway tomorrow.


Top Hotel Deals

See all 32 Hotels in South Boston
Days Inn & Suites by Wyndham South Boston $68
Days Inn & Suites by Wyndham South Boston

Days Inn & Suites by Wyndham South Boston

1074 Bill Tuck Hwy, South Boston
     
    3.6
    of 5, from 201 reviews
    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 Memorial. Clarksville Regional Museum and Prestwould Plantation are also within 32 mi (52 km).

    Fairfield Inn & Suites South Boston $124
    Fairfield Inn & Suites South Boston

    Fairfield Inn & Suites South Boston

    1120 Bill Tuck Hwy, South Boston
       
      4.4
      of 5, from 155 reviews
      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. Hudson Heritage Farms and Staunton River Battlefield State Park are also within 20 mi (32 km).

      The Berry Hill Resort & Conference Center $125
      The Berry Hill Resort & Conference Center

      The Berry Hill Resort & Conference Center

      3105 River Road, South Boston
         
        4.8
        of 5, from 87 reviews
        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 Meadows Farm Vineyard and Staunton River State Park are also within 25 mi (40 km).

        Super 8 by Wyndham South Boston VA $61
        Super 8 by Wyndham South Boston VA

        Super 8 by Wyndham South Boston VA

        1040 Bill Tuck Hwy, South Boston
           
          3.7
          of 5, from 197 reviews
          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. Hudson Heritage Farms and Staunton River Battlefield State Park are also within 20 mi (32 km).

          Quality Inn $76
          Quality Inn

          Quality Inn

          2001 Seymour Drive, South Boston
             
            3.0
            of 5, from 24 reviews
            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. Hudson Heritage Farms and Staunton River Battlefield State Park are also within 20 mi (32 km).

            Americas Best Value Inn & Suites - South Boston $49
            Americas Best Value Inn & Suites - South Boston

            Americas Best Value Inn & Suites - South Boston

            2050 Philpott Rd, South Boston
               
              2.8
              of 5, from 84 reviews
              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 Vineyards. Staunton River State Park and Staunton River Battlefield State Park are also within 25 mi (40 km).

              Oak Grove Plantation $115
              Oak Grove Plantation

              Oak Grove Plantation

              1245 Cluster Springs Rd, South Boston
                 
                5.0
                of 5, from 1 reviews
                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 Club.

                Charles Bass House Bed & Breakfast $115
                Charles Bass House Bed & Breakfast

                Charles Bass House Bed & Breakfast

                1505 North Main Street, South Boston
                   
                  4.9
                  of 5, from 39 reviews
                  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 Heritage Farms. Staunton River State Park and Staunton River Battlefield State Park are also within 20 mi (32 km).