Skip to content

South Boston vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in South Boston

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Cottage in South Boston
Lady in Red
Enjoy this cozy cottage located just minutes from Clarksville/Kerr Lake or downtown South Boston, VA. Nearby attractions include South Boston Speedway, VIR, Fit Club, Heritage Trail, downtown shopping, Busy Bean coffee shop and deli, fine dining at Molasses Grill, or lakeside at the Bridgewater Bar and Grill, Cooper’s Landing, Tunnel Creek Winery, Clarksville Brewery Company, Springfield Distillery, Factory Street Brewery, Blue Creek Cove Donuts, and Dairy Dell old fashioned hotdogs & ice cream!
$175 per night
SUPERHOST
Home in Halifax
Spencer Hill
Home Away from Home! Newly remodeled home features 3 bedrooms, 1 bath, large fully equipped kitchen, family room, and screened in patio. We are centrally located between Historic Downtown Halifax and South Boston minutes to shopping, fine dining and entertainment, Molasses Grill, Berry Hill Plantation, Factory Street Brewing, Springfield Distillery, Tunnel Creek Vineyards, short track racing at South Boston Speedway, 20 mins west is VIR race track, and Clarksville lake is 20 mins east.
$150 per night
Home in South Boston
Papa's Place at Foy's Farm
Relax with the whole family at this peaceful place to stay.... Welcome to Papa's Place! Our completely renovated 1959 two bedroom one bath home in rural South Boston VA where rustic meets modern. We invite you to enjoy the large front yard, let the butterflies greet you and make you feel warm, watch the deer grazing in the back, cherish sunsets from the front porch or late nights by the firepit. Come visit Papa's Place... where you will ALWAYS be at home!
$157 per night
SUPERHOST

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Stay near South Boston's top sights

Photo of South Boston Speedway
South Boston Speedway8 locals recommend
Photo of The Berry Hill Resort & Conference Center
The Berry Hill Resort & Conference Center5 locals recommend
Photo of Mi Carreta Mexican Grill
Mi Carreta Mexican Grill3 locals recommend
Photo of O Sole Mio Pizzeria
O Sole Mio Pizzeria3 locals recommend
Photo of Southern Plenty
Southern Plenty7 locals recommend
Photo of Tailgators Grill
Tailgators Grill3 locals recommend

Other great vacation rentals in South Boston

Rental unit in South Boston
Quiet Downtown Loft in SoBo
$115 per night
SUPERHOST
Home in Roxboro
Affordable House with Comfy Bed
$46 per night
Home in South Boston
Basement Apt. minutes from airport & Speedway!
$85 per night
SUPERHOST
Home in South Boston
Lake House on Private Lake. Extended stay
$88 per night
Home in Halifax
The Lucky Leah - Charming Home in Downtown Halifax
$200 per night
Private room in Alton
Sunnyview 1894, Owen Suite/main level
$110 per night
SUPERHOST
Private room in Alton
Sunnyview 1894, Sunset Room/upstairs
$89 per night
SUPERHOST
Place to stay in Roxboro
Original Midcentury Modern "Glass House on Hyco"
$399 per night
SUPERHOST
Home in Alton
8 mi. to VIR! 20 min to Danville, S. Boston, Hyco
$138 per night
SUPERHOST
Private room in Sutherlin
Virginia Farmland Oasis
$43 per night
SUPERHOST
Guest suite in Roxboro
Mayo Lake Front Spilt Unit: Highend,Clean,Updated
$83 per night
SUPERHOST
Private room in Alton
Sunnyview 1894, Patrick Henry Suite/upstairs
$110 per night
SUPERHOST
  1. Airbnb
  2. United States
  3. Virginia
  4. Halifax County
  5. South Boston