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 $39 SGD 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.

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Guest favourite
A spacious living area is furnished with a dark sectional sofa and a wooden coffee table atop a neutral area rug. Light fixtures hang from the ceiling, and a warm welcome sign is mounted on the wall. The open layout provides a view into the dining space.
Home in Alton
4.95 out of 5 average rating, 202 reviews

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.

Guest favourite
The kitchen and dining area features wooden walls and ceiling, complemented by natural light from a window. A spacious kitchen island with bar stools is visible, alongside a dining table surrounded by black chairs. Decor includes mounted deer heads, enhancing the rustic ambiance.
Cabin in Clarksville
4.96 out of 5 average rating, 107 reviews

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.

Guest favourite
The entrance of the studio apartment is framed by an inviting porch. Two comfortable chairs are positioned beside a small table on a gravel area. A wooden 'WELCOME' sign is attached to the exterior wall, complementing the vibrant orange siding surrounded by trees.
Flat in Halifax
4.87 out of 5 average rating, 77 reviews

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.

Top guest favourite
A welcoming entryway features double doors that open to a view of a tree-lined street. Natural light enhances the space, highlighting a plush sofa adorned with decorative cushions. A stylish lamp stands on a side table, while wall decor adds subtle character.
Home in Halifax
5 out of 5 average rating, 60 reviews

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.

Guest favourite
A spacious porch area is highlighted by three blue rocking chairs, each adding a pop of color against the natural wood decking. A decorative cushion with a paisley pattern sits on one chair, complementing the inviting outdoor space near large windows adorned with soft curtains.
Home in South Boston
4.94 out of 5 average rating, 103 reviews

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!

Guest favourite
Tiny home in Roxboro
5 out of 5 average rating, 12 reviews

The Haven- lake front, cozy tiny home, fire pit

The Haven is a newly built tiny home on Mayo lake filled with sunlight and calm. Has an airy feel that makes this the perfect spot for a quiet retreat, weekend getaway, or cozy stay near the water. Lake Front! Has everything you need- 50" TV, WIFI, Fully functional kitchen, Keurig, and more. The layout is unique: the toilet and sink are in a small enclosed bathroom, and the shower is just a couple steps away in the bedroom area. Grill and firepit area are available!

Top guest favourite
Home in Semora
4.96 out of 5 average rating, 27 reviews

Sunset Lakefront Glass Retreat, Hot Tub, Kayaks

Just an hour from RTP, this sunset lakefront retreat is designed around the view, with expansive glass walls that bring Hyco Lake right into the living space. Spend the day on the water—launch a kayak, cast a line from the private dock, or relax by the lake—then unwind in the hot tub or around the fire pit as the sky turns gold. Perfect for romantic getaways, girls' weekends, or a peaceful midweek reset. Fast WiFi makes remote work easy, with on-site EV charging.

Top guest favourite
Home in Semora
5 out of 5 average rating, 16 reviews

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.

Top guest favourite
Home in South Boston
4.93 out of 5 average rating, 30 reviews

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.

Guest favourite
Flat in South Boston
5 out of 5 average rating, 23 reviews

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.

Guest favourite
The log cabin is surrounded by lush greenery, with vibrant azaleas in full bloom occupying the foreground. A welcoming porch features bench seating, and large windows provide natural light. The sloped roof with gables adds architectural interest, set against a backdrop of trees.
Cabin in Roxboro
4.94 out of 5 average rating, 138 reviews

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!

Guest favourite
The exterior of a welcoming single-story home is highlighted, featuring a red roof and a spacious front porch. Lush greenery surrounds the property, enhancing the tranquil setting. A paved driveway leads to the home, providing access to its inviting facade.
Home in Alton
4.94 out of 5 average rating, 159 reviews

Guest House near VIR, Hyco Lake, Dan River.

Enjoy this privately located home tucked into a cove of trees. Just 7 miles to VIR. A 17 mile drive brings you to Dan Daniels Memorial Park which offers beautiful, scenic, and paved walking trails, biking and fishing. (Bike & canoe rentals available at the park) The Hyco lake Marina in NC is only 9.5 miles away. Shopping and restaurants as close as a 10 minute drive.

Popular amenities for South Boston holiday rentals

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 wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

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