
Holiday rentals in South Boston
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Quick stats about holiday rentals in South Boston

Total holiday rentals
Explore 20 holiday rentals in South Boston

Nightly prices starting at
South Boston holiday rentals start at €26 per night before taxes and fees

Verified guest reviews
Over 350 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of South Boston holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across South Boston rentals

4.9 Average rating
South Boston stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated holiday rentals in South Boston
Guests agree: these stays are highly rated for location, cleanliness and more.

8 mi. to VIR! 18 min to Danville, South Boston, Va
Spacious, clean, & relaxing, this home is less than 8 miles from VIR and 18 mi to Danville, South Boston, or Roxboro. The listing is on one floor level to accommodate those with mobility issues. High-speed Starlink WiFi. Bedrooms provide linens/pillows/blankets. Bathrooms provide towels & necessities. Full kitchen w/coffee. Oversized paved parking with easy accessibility. Perfect for trailers/multiple large vehicles. Close to hwy, may want to pack earplugs. Strict no smoking or pets please.

Spacious Woodland Cabin - Kerr Lake
Calling all nature lovers, outdoors men, women, & families looking for adventure! Take a hike or enjoy the hot tub. Wooden Cabin close to Clarksville & Bluestone Landing. Take a walk or a golf cart ride to reach the property’s dock or sit on the porch & unwind. Close to everything, yet far away. Enjoy a beautiful cabin w/ modern amenities such as Starlink Internet & smart TVs throughout. Best Wi-Fi you can get -2 bedrooms, 2 full baths, rec room & loft w/4 beds. The perfect place to disconnect.

Acorn Acre
Acorn Acre is a cozy and stylish 1 bedroom studio apartment nestled away in the oak trees! This cozy space is perfect for solo travelers or couples looking for a comfortable and stylish place to stay. The apartment is filled with natural light and features colorful decor. The kitchen is fully equipped with everything you need, and the bathroom is modern and clean. Centrally located between Historic Downtown Halifax and South Boston minutes to shopping, fine dining and entertainment.

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!

Glass House on the Lake
This midcentury modern retreat nestled in a relaxing cove features floor-to-ceiling glass walls allowing the outdoors in, beautiful exposed wood beams, hardwood floors, and a cozy concrete fireplace. Enjoy the screened porch with new comfortable seating, updated kitchen, and stunning lake views. The gentle slope to the private dock passes by numerous resting nooks. Convenient to the Triangle, Triad, and VIR, it’s the perfect getaway blend of relaxation and adventure.

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.

Quiet Downtown Loft
Loft apartment in downtown South Boston VA, perfect for longer term stays. Appropriate discounting available for week or month long bookings. Five miles from Molasses Grill in Halifax VA. Five minutes from South Boston Speedway. Less than ten minutes from Berry Hill Resort and Springfield Distillery. And only 20 minutes from Virginia International Raceway. Street entrance to upstairs loft. Above quiet professional office space.

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.
Popular amenities for South Boston holiday rentals
Other great holiday rentals in South Boston

Mollie's Lakehouse

Cousin Carol's Fishing Adventure! Scottsburg, VA

The Silo at Lake Front Winery

Hyco Horizon, Boat Tie, Calm Cove, Outdoor Vibes

Hummingbird Hollow at Lake Hyco

Oak Heights Farmhouse

BohoNook

Sunset Lakefront Glass Retreat, Hot Tub, Kayaks
Frequently Asked Questions
Are there family-friendly vacation rentals in South Boston?
South Boston has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in South Boston?
Experience the best of South Boston with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in South Boston?
Yes! Work meets play with ease at over 10 vacation rentals in South Boston featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in South Boston have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in South Boston. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in South Boston have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in South Boston. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in South Boston have wifi?
Absolutely! We offer over 10 house rentals with wifi in South Boston. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in South Boston have free parking?
Absolutely! We offer over 10 house rentals with free parking in South Boston. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in South Boston?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
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- Smith Mountain Lake State Park
- Duke University
- Virginia International Raceway
- Sarah P. Duke Gardens
- Durham Bulls Athletic Park
- Eno River State Park
- American Tobacco Campus
- Duke Chapel
- Liberty Mountain Snowflex Centre
- Durham Farmers' Market
- Carolina Theatre
- Occoneechee Mountain State Natural Area
- Museum of Life and Science
- Durham Performing Arts Center
- Appomattox Court House National Historical Park
- The Durham Hotel
- 21c Museum Hotel
- Falls Lake State Recreation Area
- SeaQuest Lynchburg
- West Point On The Eno
- Durham Central Park





