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Holiday houses in South Boston

Find and book unique accommodation on Airbnb

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
4.94 out of 5 average rating, 199 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.

Top 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, 106 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.

Top Guest favourite
An open-plan interior features a king size bed with a light-colored bedspread in the foreground. A cozy seating area with a loveseat and coffee table is situated next to the kitchenette, which includes modern appliances and a window allowing natural light to fill the space.
Treehouse in Bedford
5 out of 5 average rating, 154 reviews

Cross Creek Luxury Couples Cabin

Cross Creek Luxury Couples Cabin is a one of a kind, romantic, get-away for two just 3 miles from the Blueridge Parkway. From its uniquely designed suspension over top of a creek, lighted boardwalk path through the woods that ramps up to the cabin amongst the trees giving it a true tree-house feel, 3 spacious decks for lounging and enjoying nature and the sounds of the roaring creek beneath you, to luxurious amenities galore inside and out. All in a secluded, private setting minutes from town!

Top Guest favourite
A modernized cabin is set in a serene natural environment, surrounded by green grass and trees. A covered porch is featured at the front, with rocking chairs and a porch swing positioned for relaxation. A pathway leads to the cabin, enhancing accessibility.
Cabin in Long Island
4.92 out of 5 average rating, 106 reviews

100acre Woods Cabin Retreat

No Smoking in home, No animals or pets allowed! 30 mi to Lynchburg, 11 to Altavista. This cabin boasts 100 acres of serene nature while hiking the trails, fishing and swimming in the river. Canoe from the boat slip down river to the long Island community center. Relax on the large rocking chair front porch with your honey on the porch swing, or roast marshmallows and sip drinks around the fire pit! This is not a party house, it is meant to relax and enjoy peace, quiet, and nature, enjoy!

Guest favourite
Home in Halifax
4.91 out of 5 average rating, 147 reviews

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.

Top Guest favourite
A rustic cabin is presented with a welcoming porch supported by sturdy posts. Steps lead up to the entrance, where the surrounding greenery and trees provide a natural setting. An American flag hangs nearby, contributing to the serene atmosphere of the property.
Cabin in Roxboro
4.88 out of 5 average rating, 190 reviews

Water Front Lake House!

Waterfront home on MAYO LAKE. 2 Bd, 1.5 bath fully furnished . Wi-fi, Smart TVs, Alexa, frig, stove washer/dryer, microwave. Queen-size bed, sleeper sofa and bunk bed. Wrap around porch w/ rocking chairs, swing and 2 picnic tables. Large yard for playing, just feet away from the water and dock, hammock and fire pit. Lots of fishing, single kayak, 2 person kayak, canoe and 2 paddle boats available. PERFECT FOR ANY SEASON LONG OR SHORT STAY. Located on Mayo Lake in Roxboro, NC

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, 57 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
4.95 out of 5 average rating, 100 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!

Top Guest favourite
A serene lake is observed from a wooden dock, with calm waters reflecting surrounding greenery and a clear sky. The shoreline is lined with trees, creating a tranquil atmosphere. Ripples gently disturb the water's surface, highlighting the lake's peaceful environment.
Home in Roxboro
4.98 out of 5 average rating, 107 reviews

Long’s Lakehouse

Relax with the whole family at this peaceful waterfront property. It is a 2 bedroom, 2 bathroom house with one king bed, one queen bed, and a pull out sofa! The kitchen is fully stocked with a coffee pot, utensils, pizza pan, crock pot, skillet, pots , pans, baking sheets, toaster, oven and microwave! Bedrooms and living room have smart tvs. WiFi available! Enjoy the kayaks, lots of fishing, grilling, and fire pit! There is something for here for everyone!

Top Guest favourite
Home in South Boston
4.93 out of 5 average rating, 27 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
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, 135 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
A cozy bedroom is presented with a spacious bed covered in a deep red blanket. Two bedside lamps provide soft lighting beside the bed, and a decorative bench sits at the foot. Hardwood flooring and a patterned area rug complement the room's neutral walls and window treatments.
Home in South Boston
4.85 out of 5 average rating, 47 reviews

Brightleaf- Comfortable & Spacious 3 Bed / 2 Bath

Your whole group will enjoy easy access to everything from this centrally located pet-friendly home in a quiet neighborhood. Our home features three bedrooms, with a pull out sofa, and a futon allowing comfortable sleeping for 8. There’s also plenty of space to spread out both inside and outside as there is an additional den and covered porch with fenced in yard. We would love for you to visit!

Popular amenities for South Boston holiday rentals

Frequently Asked Questions

  • 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.

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 $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 310 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of South Boston holiday 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!

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