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South Boston vacation rentals

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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!
$160 per night
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
Lake House on Private Lake. Extended stay
Paradise Hotel Alternative for business people staying 1 to 6 months in privacy. Beautiful lake house with full kitchen & living room, separate bedroom & porch for relaxing in your space enjoying the peaceful views & wildlife. In our private gated home place. Perfect for temporary travelers in Medical, Healthcare, Power, Energy, Engineers, Tech & Personnel fields sense it is only 3 miles from downtown. Close to everything, but you feel miles from civilization, the best of both worlds.
$88 per night

Stay near South Boston's top sights

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 South Boston Speedway
South Boston Speedway8 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

Guesthouse in Halifax
Hunter's Retreat at Springfield 1842
$150 per night
Home in Halifax
Tay's House
$125 per night
Home in Halifax
The Lucky Leah - Charming Home in Downtown Halifax
$200 per night
Guest suite in Roxboro
Mayo Lake Front Spilt Unit: Highend,Clean,Updated
$83 per night
Home in South Boston
Papa's Place at Foy's Farm
$170 per night
Private room in Sutherlin
Virginia Farmland Oasis
$43 per night
Place to stay in Roxboro
Original Midcentury Modern "Glass House on Hyco"
$399 per night
Private room in Alton
Sunnyview 1894, Owen Suite/main level
$110 per night
Home in Leasburg
Mountain cabin feel on Hyco Lake. 20 mins to VIR!
$125 per night
Home in South Boston
Basement Apt. minutes from airport & Speedway!
$85 per night
Private room in Halifax
Classy 1 bedroom & bath/shower suite in home
$59 per night
Cottage in Clarksville
Meremont on the Lake
$117 per night
  1. Airbnb
  2. United States
  3. Virginia
  4. Halifax County
  5. South Boston