Holiday rentals in South Boston

Dockside Dreamz #1 with Deep Water Dock

The downstairs unit of this lakefront duplex offers stunning main lake views, a private dock, fire pit and sandy beach (normal pool), all just minutes from downtown Clarksville. Whether you’re fishing Buggs Island/Kerr Lake, vacationing with family, relaxing on the patio, or checking out the local wineries and brewery, Dockside Dreamz #1 is the perfect escape with all the comforts of home. Sleeps six, Wi-Fi, grill, and a large patio. Discounts available for those also renting Dockside Dreamz #2.

8 mi. to VIR! 18 min to Danville, South Boston, Va

Spacious & relaxing, this rural country home is 8 miles from VIR, and ~18 mi to Danville, South Boston, & Roxboro. The listing is on one floor level. High-speed Starlink WiFi. Bedrooms have linens/pillows/blankets. Bathrooms have towels,soap, etc. Full kitchen with coffee. Oversized paved parking with easy accessibility. Perfect for trailers/multiple large vehicles. Close to hwy, may want to pack earplugs. Please note: this listing is not in the city. Strict no smoking or pets please.

Lakefront Oasis-HotTub|Sauna|GameRoom|Kayaks|Dock

At Pointe Mayo Lake, discover a serene, rustic retreat by Mayo Lake. Enjoy amenities like kayaks & canoes, private dock, fishing rods, a cedar barrel sauna, a grill, a hot tub, a game room, and a fire pit. Perfect for avid vacationers, couples, families, groups of professionals, and even your furry friends! We are Pet and Family Friendly! Love what you see but not ready to book? Click the ❤️ "Save" button on the top right to easily find us again and secure your getaway when you're ready!

Spencer Hill

Home Away from Home! Spencer Hill 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.

The Lucky Leah - Charming Home in Downtown Halifax

Welcome to the Lucky Leah! Enjoy this newly renovated home built in 1900 located in the heart of Historic Downtown Halifax. The flow and function of this home will work for families of all sizes. This home sleeps 6 guests and features spacious 2 Bedrooms 2 Bathrooms including a queen size sleeper sofa . Only footsteps away from Molasses Grill and a short drive to Tunnel Creek Vineyards, Factory Street Brewing, and Springfield Distillery, and located only 20 miles from VIR.

Pastoral Retreat: Embracing Equines, Cows & Nature

Escape to this serene retreat, where comfort meets nature. The home features 3 cozy bedrooms, 2 modern bathrooms, and ample space for six guests. Relax in the inviting living area, cook in the fully equipped kitchen, or explore the 300-acre property with hiking trails and an equestrian facility. This nonsmoking house ensures a fresh environment, with a $150 fee for any violations. Book now to experience the perfect blend of comfort and adventure in a truly special setting.

Papa's Place at Foy's Farm

Relax with the family, friends, or solo... Welcome to Papa's Place! Our completely renovated 1959 two bedroom one bath home in South Boston VA where rustic meets modern. We invite you to enjoy the large front yard, let the butterflies greet you, watch the deer graze, cherish sunsets from the front porch or late nights by the firepit. Only 26 miles from VIR and 30 from the NEW CEASARS VIRGINIA CASINO!! Come visit Papa's Place... where you will ALWAYS be at home!

Lake Front | Beautiful Views | Perfect Getaway

Come find a place of rest, relaxation and renewal here at Still Waters. A place that has been built by the hands of its owners, bringing peace to everyone that enters the home. This custom built home is situated just on the waters edge, with a dock and canoes available for use. This home is perfect for a couples get away, looking to recharge away from the hustle and bustle of our everyday lives. Roxboro is about 25 minutes away from the home.

Farm Life, Close to Town

Relax in this beautiful rural setting while remaining super close to town. Fully remodeled, this home has all up to date amenities, stylish furniture and fixtures, cleanliness and tranquility, all within minutes of the most popular attractions in South Boston and Clarksville. Perfect for work or travel, or just to explore a new area for a bit, we welcome you to come and relax on our deck at sunset and see why we love it so much here.

Majestic Lakefront Log Cabin in the NC High Plains

Cozy Log Cabin located on Lake Mayo just above Roxboro, North Carolina on Whispering Wolf Ranch. Easy access to a functional floating dock. Great for fishing, swimming, meditating, or to just enjoy nature. Paddle boards and Kayaks can be rented at nearby Mayo Lake Park. Can be used for a private romantic getaway or family retreat. Less than 5 miles from the events held at Lake Mayo Park. PARTIES OR EVENTS ARE NOT ALLOWED!

Bannister Farm

On the historic registry in a lovely small town setting close to VIR, Berry Hill plantation, award winning dining at Molasses, brewery and restaurants in Halifax and South Boston, and a 30 minute drive to Danville or Buggs Island Lake. 150 year old original farm house beautifully decorated. but still 150 years old!! The space is a duplex, not quite half the house. It is the side to the right as you face the house.

Uncle Nelson's Woodland Hideaway! Scottsburg, VA

Welcome to the Woodland Hideaway at the Little Tin Can Campground! Come rest, relax and enjoy the charming little town of Scottsburg, VA! This cozy-cabin has been completely renovated and is just minutes away from fishing, hiking and outdoor activities at Staunton River State park; situated close to South Boston and the Speedway; and about 20-30 min away from several wineries.