Vacation rentals in South Boston

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in South Boston

  • Total vacation rentals

    Explore 20 vacation rentals in South Boston

  • Nightly prices starting at

    South Boston vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

  • Verified guest reviews

    Over 350 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of South Boston vacation rentals include wi-fi 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 vacation rentals in South Boston

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

1 of 1 pages1 / 1
Guest favorite
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
4.94 out of 5 average rating, 206 reviews

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.

ValueLocationCondition

Guest favorite
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.
Apartment in Halifax
4.88 out of 5 average rating, 85 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.

LocationFamilyOutdoor spaces

Top guest favorite
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, 62 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.

FamilyLocationCheckout

Guest favorite
A curious dog observes a herd of grazing cattle in a lush green field. The cows, in various shades of brown and black, are scattered throughout the expansive landscape, surrounded by tall grass and a clear blue sky.
Home in Halifax
4.93 out of 5 average rating, 42 reviews

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.

ValueLocationGetting around

Guest favorite
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, 105 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!

FamilyLocationView

Top guest favorite
A private dock is set against calm waters, with two green Adirondack chairs positioned for relaxation. The surrounding area features tree-lined shores and a clear blue sky, enhancing the peaceful lakeside atmosphere.
Home in Clarksville
5 out of 5 average rating, 50 reviews

Kerr Lake Escape | Dock + Beach Access

One of the few Kerr Lake rentals located right in Clarksville. Party in Slow Motion is a beautifully decorated 3BR/2BA lake cottage near Clarksville with views of Buggs Island/Kerr Lake. Located just one row back from the water, it’s an easy ~100 yard walk to our private slip dock and quiet beach access in a calm cove. Two kayaks are included for exploring the lake. Ideal for families, fishermen, and small groups, with high-speed Wi-Fi and air conditioning.

LocationFamilyIndoor spaces

Top guest favorite
Home in South Boston
4.94 out of 5 average rating, 32 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.

FamilyLocationLong stay

Guest favorite
Apartment 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.

ValueLocationIndoor spaces

Superhost
A sunlit sunroom features a wicker seating area adorned with blue and green cushions. A small table sits in the center, complemented by a potted plant. Large windows frame the view of the expansive backyard, allowing natural light to fill the space.
Home in Halifax
4.74 out of 5 average rating, 31 reviews

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.

LocationBathroomAccuracy

Guest favorite
Home in Semora
4.94 out of 5 average rating, 32 reviews

Sunset Lakefront Glass Retreat, Hot Tub, Kayaks

Just an hour from RTP, this private lakefront retreat is designed around the view, with soaring ceilings and expansive glass walls overlooking Hyco Lake. Paddle from the private dock, relax in the hot tub, gather around the fire pit, and watch the sunset from the great room. Ideal for couples, families, friends, and peaceful getaways, with fast Wi-Fi and on-site EV charging.

FamilyLocationWifi

Guest favorite
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, 163 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.

LocationFamilyDecor

Superhost
Home in South Boston
4.77 out of 5 average rating, 140 reviews

Country Home

This Country Home is located in a private area of South Boston, Va. Conveniently 10 mins from major food chains and shopping centers. Its 30 mins from VIR Race Track and 5 mins away from South Boston Speedway. Its also located in 30-40 mins from Duke University, Occeecheen State Park, and Avery College. This home is also pet friendly , for your furry friends.

FamilyValueAccuracy

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