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South Boston, VA vacation rentals
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Best Vacation rentals and Airbnb offers in South Boston, VA

Top Vacation Rentals for Families in South Boston, VA

These kid-friendly vacation rentals in South Boston, VA keep you close to top city attractions for a stress-free family vacation.

Charming Remodeled Historic Home In The Small Town Of South Boston, Virginia. - South Boston, VA
10 6 reviews
South Boston, VA
08/22 – 09/04
$203/nighttotal: $2639 (13 )

Charming Remodeled Historic Home In The Small Town Of South Boston, Virginia.

2 2
apartment , South Boston
This charming 2-bedroom apartment in South Boston, Virginia, is conveniently located near the Staunton River Battlefield State Park and Prestwould Plantation, both within a short drive. Enjoy the peaceful ambiance of this historic town with its rich history and natural beauty.
This comfortable rental offers a private bathroom in each unit, accommodating up to 6 guests. Enjoy amenities like air conditioning, an ironing board and iron, and close proximity to Mayo Lake and Hudson Heritage Farms for outdoor activities.
2 Mi To South Boston Speedway: Cozy Tiny Home! - South Boston, VA
South Boston, VA
08/22 – 09/04
$188/nighttotal: $2444 (13 )

2 Mi To South Boston Speedway: Cozy Tiny Home!

1 2
apartment , South Boston
This South Boston apartment rental is conveniently located near North Main Street Park and Grove Park, offering easy access to nearby water activities and day trips to Green's Folly Golf Course and Greenwood Winery.
This 360-square-foot unit features one bedroom, one bathroom, and accommodates two guests, boasting a fully equipped kitchen, air conditioning, on-site parking, and access to a garden and spa.
The Berry Hill Resort & Conference Center - South Boston, VA
9.2 729 reviews
South Boston, VA
08/06 – 08/07
$206/nightfor 1 night

The Berry Hill Resort & Conference Center

1 2
resort , South Boston
The Berry Hill Resort & Conference Center is located in South Boston's historic district, just a short drive from Sentara Halifax Regional Hospital, the L. E. Coleman African-American Museum, and South Boston Speedway. The resort has received excellent ratings for its location, cleanliness, and overall user experience.
The hotel features an indoor pool, a fitness center, and a sauna, along with a full-service spa offering a variety of treatments. Guests can enjoy free continental breakfast, Wi-Fi, and parking, as well as dine at the resort's two restaurants and bars.

Best South Boston, VA vacation rentals with parking

2 Mi To South Boston Speedway: Cozy Tiny Home! - South Boston, VA
South Boston, VA
08/22 – 09/04
$182/nighttotal: $2366 (13 )

2 Mi To South Boston Speedway: Cozy Tiny Home!

1 2
house , South Boston
This South Boston vacation rental is conveniently located near Lynchburg, approximately 55 miles from Lynchburg Regional Airport, offering easy access to area attractions. This 360-square-foot house features one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen, spa, parking, and free Wi-Fi.
12 Mi To Staunton River State Park: Off-grid Cabin - South Boston, VA
10 2 reviews
South Boston, VA
08/22 – 09/04
$125/nighttotal: $1625 (13 )

12 Mi To Staunton River State Park: Off-grid Cabin

1 2
cabin , Scottsburg
This Scottsburg, Virginia cabin, located off Route 360, offers easy access to South Boston Speedway (5 miles away), Occoneechee State Park (30 miles), and Greens Folly Golf Course (8 miles).
This 750-square-foot getaway sleeps four, features a one-bedroom, one-bathroom layout, a wood-burning stove, campfire pit, charcoal grill, and a well-equipped kitchenette; enjoy nearby hiking, fishing, and boating opportunities.

Frequently Asked Questions about vacation rentals in South Boston, VA

  • Which walking or cycling routes are the best in South Boston, VA?

    The Tobacco Heritage Trail is a great option for both walking and cycling. It runs for 11 miles along the former Norfolk Southern Railway line, offering scenic views of the countryside. You can also enjoy a walk or bike ride around the South Boston Town Common.
  • What are the best Airbnb and vacation rentals in South Boston, VA?

    Basement Apt - Minutes From Airport & Speedway, Quiet Downtown Loft and Quiet Downtown Apartment are the most popular Airbnb and vacation rentals in South Boston, VA among travelers.

  • What sports or outdoor activites can visitors enjoy in and around South Boston, VA?

    South Boston is a great place to enjoy outdoor activities. You can go fishing at John H. Kerr Reservoir, play golf at the South Boston Golf Club, or go hiking at Staunton River State Park.
  • What are the most popular Airbnbs in South Boston, VA?

    Among the Airbnbs in South Boston, VA, Basement Apt - Minutes From Airport & Speedway, Quiet Downtown Loft and Quiet Downtown Apartment are the most popular ones.

  • What amenities are commonly available in vacation rentals in South Boston, VA?

    Vacation rentals in South Boston usually have basic amenities like Wi-Fi, air conditioning, and a fully equipped kitchen. Some rentals may also offer extras like a pool, hot tub, or fire pit.
  • What are the best rentals for families and kids in South Boston, VA?

    Basement Apt - Minutes From Airport & Speedway and Home Sweet Home are the best vacation rentals for families and kids in South Boston, VA.

  • What time of year is best to rent a vacation rental South Boston, VA?

    The best time to visit South Boston is during the spring or fall. The weather is mild, and there are fewer crowds. You can also enjoy the beautiful fall foliage in the fall.
  • What are the local dishes in South Boston, VA region?

    South Boston is known for its Southern cuisine. Some of the local dishes you should try include fried chicken, barbecue, and hushpuppies. You can also find plenty of fresh seafood, especially during the summer months.

Destinations nearby

Best Vacation Rentals with Balconies in South Boston, VA

Start your morning right with a vacation rental in South Boston, VA featuring a private balcony and stunning views.

12 Mi To Staunton River State Park: Off-grid Cabin - South Boston, VA
South Boston, VA
08/22 – 09/04
$133/nighttotal: $1729 (13 )

12 Mi To Staunton River State Park: Off-grid Cabin

1 2
cabin , Scottsburg
This Scottsburg, Virginia cabin rental is located approximately 58 miles from Lynchburg Regional Airport, offering easy access to local attractions.
This 750-square-foot house features one bedroom, one bathroom, a fully equipped kitchen (including a fridge and microwave), air conditioning, a garden, parking, and can comfortably accommodate up to seven guests.
The Berry Hill Resort & Conference Center - South Boston, VA
9.2 729 reviews
South Boston, VA
08/06 – 08/07
$206/nightfor 1 night

The Berry Hill Resort & Conference Center

1 2
resort , South Boston
The Berry Hill Resort & Conference Center is located in South Boston's historic district, just a short drive from Sentara Halifax Regional Hospital, the L. E. Coleman African-American Museum, and South Boston Speedway. The resort has received excellent ratings for its location, cleanliness, and overall user experience.
The hotel features an indoor pool, a fitness center, and a sauna, along with a full-service spa offering a variety of treatments. Guests can enjoy free continental breakfast, Wi-Fi, and parking, as well as dine at the resort's two restaurants and bars.

Our Favorite Pet-Friendly Vacation Rentals in South Boston, VA

Travel with ease to South Boston, VA with pet-friendly rentals located near local dog parks and scenic city walks.

Cozy 3br Virginia Home Near Historic Berry Hill - South Boston, VA
South Boston, VA
08/22 – 09/04
$150/nighttotal: $1950 (13 )

Cozy 3br Virginia Home Near Historic Berry Hill

3 2
apartment , South Boston
This South Boston condominium offers a relaxing retreat in South Central Virginia, providing easy access to the area's historical sites and natural beauty.
This single-level residence accommodates up to six guests with three bedrooms and one bathroom, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, plus air conditioning and internet for your convenience.
Bohonook - South Boston, VA
10 18 reviews
South Boston, VA
08/22 – 09/04
$156/nighttotal: $2028 (13 )

Bohonook

1 2
apartment , Halifax
This Halifax Airbnb rental is conveniently located in a quiet, family-friendly neighborhood, a short drive from downtown Halifax, Sentara Halifax Regional Hospital, and numerous shopping and dining options including Walmart, Lowe's, and Food Lion.
This pet-friendly two-bedroom, one-bathroom apartment sleeps four, offering a queen bed, futon, and sofa, two desks, a full kitchen, air conditioning, parking, and Wi-Fi; nearby amenities include The Fit Club, the YMCA, a walking/biking trail, and a golf course.
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