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 Packages

Each and every destination possesses its own unique charms. South Boston is certainly no exception.

Save Time and Money with a South Boston Package Deal

Save money when you purchase accommodation and flight deals via Expedia. Getting your preferred flights and lodgings are the ingredients for a good vacation. Combining them together with us into one easy package is a sure-fire recipe for success that leaves out the stress and saves money. What are you and that special someone going to buy in South Boston with all that extra cash?

Receive savings of as much as $583 with a package deal.

Search through our global database of 400 airline partners and 321,000 hotels worldwide.

Your South Boston excursion will feel that much better with Expedia's prices.

If you have to change your vacation plans we will certainly honor your cancellation request with no extra fee, on almost all bookings.

South Boston Vacation Packages

Approximately 65 miles to the south of South Boston is the city of Raleigh, while just 95 miles to the north you'll find Charlottesville.

If you enjoy exploring Mother Nature, visit a couple of the region's natural areas. Occoneechee State Park is located 25 miles from South Boston, while Staunton River Battlefield State Park sits 17 miles away.

Sports fans will appreciate the atmosphere at Legion Field. It's in Danville, about 30 miles to the west of South Boston. You'll have to shout your lungs out with the passionate locals.

Halifax and Cluster Springs are just two of the many other places worth checking out while you're in the region. They're 4 miles and 5 miles away, respectively.

Head 20 miles east from South Boston to arrive in Clarksville. There's lots to see and do there, such as Parker Sydnor Cabin, Kinderton Country Club and Clarksville Regional Museum. Prestwould Plantation and Mecklenburg County Veterans Memorial are also cool options if you're still looking for more.

In order to truly grasp the essence of Southern Virginia, you'll need to accustom yourself with its signature scents and flavors.

Peas and okra are a couple of noteworthy ingredients that you'll get to know, if you don't already!

Enjoy the spirit of national pride on the 4th of July for Independence Day.

When you're ready to catch your flight, keep in mind that the nearest airport is 45 miles to the north.

Accommodation in South Boston

Don't expect to find a huge range of hotels near South Boston, so be sure to explore the information and deals on Expedia's hotels guide.

The Fairfield Inn & Suites South Boston and Days Inn & Suites South Boston are the main lodgings in and around South Boston.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


Top Hotel Deals

See all 31 Properties in South Boston
Days Inn & Suites by Wyndham South Boston $64
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 205 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 $119
    Fairfield Inn & Suites South Boston

    Fairfield Inn & Suites South Boston

    1120 Bill Tuck Hwy, South Boston
       
      4.4
      of 5, from 157 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 $133
      The Berry Hill Resort & Conference Center

      The Berry Hill Resort & Conference Center

      3105 River Road, South Boston
         
        4.7
        of 5, from 89 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 199 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 $72
          Quality Inn

          Quality Inn

          2001 Seymour Drive, South Boston
             
            3.1
            of 5, from 26 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 $51
            Americas Best Value Inn & Suites - South Boston

            Americas Best Value Inn & Suites - South Boston

            2050 Philpott Rd, South Boston
               
              2.8
              of 5, from 86 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, this bed & breakfast is 9 mi (14.5 km) from South Boston Speedway and within 20 mi (32 km) of Roxboro Country Club and Hudson Heritage Farms. Person County Museum and Kirby Cultural Arts Complex are also within 20 mi (32 km).

                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 40 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).

                  Top Flight + Hotel Deals

                  Top Deals on Flights

                  These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.