Vacation rentals in South Boston

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Top-rated vacation rentals in South Boston

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

Guest favorite

Cottage in South Boston

5.0 out of 5 average rating, 108 reviews

Lady in Red

Enjoy this cozy cottage located just minutes from Clarksville/Kerr Lake or downtown South Boston, VA. Nearby attractions include South Boston Speedway, VIR, Fit Club, Heritage Trail, downtown shopping, Busy Bean coffee shop and deli, fine dining at Molasses Grill, or lakeside at the Bridgewater Bar and Grill, Cooper’s Landing, Tunnel Creek Winery, Clarksville Brewery Company, Springfield Distillery, Factory Street Brewery, Blue Creek Cove Donuts, and Dairy Dell old fashioned hotdogs & ice cream!

Nov 27 – Dec 4

G$38,057 GYD per night
Guest favorite

Cabin in Blackstone

4.98 out of 5 average rating, 132 reviews

Rustic secluded cabin at Whetstone Creek Farm

Unwind in your own forest retreat. Enjoy waking up in the king size bed to views of trees, a well appointed open floor plan, and a front porch made for sitting! Listen to rain on the tin roof or enjoy a bonfire in the fire pit after taking a stroll down 2 miles of wooded trails or wading in the creek. Stay connected with high speed wifi. Wildlife abounds on our woodland plant farm. Approximately 15 minutes from Ft. Barfoot, this is the perfect place to stay in Blackstone if you want to get away!

Nov 2 – 9

G$27,143 GYD per night
Guest favorite

Home in Alton

4.92 out of 5 average rating, 112 reviews

7 mi. to VIR! 18 min to Danville, South Boston, Va

A blend of modern and traditional, this home is under 7 miles from VIR; 18 to Danville, South Boston, or Roxboro. Initial entry reveals an open floor plan combining living, dining, and kitchen areas that are comfortable, spacious, and inviting. Bed and bath spaces are clean, furnished, and stocked with linens, etc; waiting for you to settle in and recharge. Satellite WiFi. Oversized paved parking for guests; very accessible for trailers and/or multiple large vehicles. Strict no smoking or pets

Jul 2 – 9

G$41,491 GYD per night

Popular amenities for South Boston vacation rentals

Stay near South Boston's top sights

South Boston Speedway8 locals recommend
The Berry Hill Resort & Conference Center5 locals recommend
Mi Carreta Mexican Grill3 locals recommend
O Sole Mio Pizzeria3 locals recommend
Southern Plenty7 locals recommend
Tailgators Grill3 locals recommend

Other great vacation rentals in South Boston

Guest favorite

Guesthouse in Saxapahaw

4.92 out of 5 average rating, 689 reviews

The Yurt at Frog Pond Farm

Feb 18 – 25

G$24,731 GYD per night
Guest favorite

Home in Halifax

4.88 out of 5 average rating, 16 reviews

Bannister Farm

Aug 23 – 30

G$17,694 GYD per night
Guest favorite

Home in South Boston

4.98 out of 5 average rating, 51 reviews

Papa's Place at Foy's Farm

Dec 19 – 26

G$32,708 GYD per night
Guest favorite

Home in Halifax

4.97 out of 5 average rating, 31 reviews

Tay's House

May 23 – 30

G$29,063 GYD per night
Guest favorite

Cabin in South Boston

5.0 out of 5 average rating, 6 reviews

Lakefront Cabin

Sep 12 – 19

G$29,454 GYD per night
Guest favorite

Home in Halifax

5.0 out of 5 average rating, 24 reviews

"The Guest House of Halifax"

Jan 2 – 9

G$30,250 GYD per night
Guest favorite

Home in Halifax

5.0 out of 5 average rating, 21 reviews

The Lucky Leah - Charming Home in Downtown Halifax

Jul 24 – 31

G$42,252 GYD per night
Guest favorite

Home in Clarksville

4.95 out of 5 average rating, 43 reviews

Country Living near Buggs Island/Kerr Lake

May 6 – 13

G$24,528 GYD per night
Guest favorite

Home in Roxboro

5.0 out of 5 average rating, 25 reviews

Long’s Lakehouse

Jul 13 – 20

G$30,894 GYD per night
Guest favorite

Tiny home in Hillsborough

4.99 out of 5 average rating, 83 reviews

Cozy School Bus Getaway - 15 minutes to Duke!

May 19 – 24

G$24,789 GYD per night
Guest favorite

Apartment in Clarksville

4.98 out of 5 average rating, 91 reviews

Cozy Getaway Efficiency on Buggs Island/Kerr Lake

Sep 25 – Oct 2

G$31,316 GYD per night
Guest favorite

Apartment in Clarksville

5.0 out of 5 average rating, 20 reviews

Gilliland Hotel 1898

Sep 6 – 13

G$25,778 GYD per night

Quick stats about vacation rentals in South Boston

Total rentals

10 properties

Popular amenities

Gym, BBQ grill, and Laptop-friendly workspace

Wifi availability

10 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Total number of reviews

110 reviews

Nightly prices starting at

G$4,188 GYD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Halifax County
  5. South Boston