Holiday rentals in South Boston

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Top-rated holiday rentals in South Boston

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

Guest favourite

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!

20–27 Nov

₹15,149 per night
Guest favourite

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!

22–29 Jan

₹9,508 per night
Guest favourite

Farm stay in Greensboro

4.95 out of 5 average rating, 198 reviews

Arya’s cottage with a loft & jacuzzi

Adults only, 18&older. No smoking or vaping allowed inside or on premises. Up to 2 dogs welcome for an additional fee. Peaceful and centrally-located place. From your loft bedroom overlook beautiful rolling pastures. Take a stroll on our walking trails or through the woods on the 41 acres, read a book, sit around your fire pit, soak in the private jacuzzi, or head 6 miles to downtown for some nightlife. We do offer a tour and interaction with the animals for an additional fee and scheduled time.

5–12 Aug

₹9,600 per night

Popular amenities for South Boston holiday 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 holiday rentals in South Boston

Guest favourite

Home in South Boston

4.98 out of 5 average rating, 51 reviews

Papa's Place at Foy's Farm

10–17 Nov

₹13,020 per night
Guest favourite

Home in Halifax

4.97 out of 5 average rating, 31 reviews

Tay's House

23–30 May

₹11,569 per night
Guest favourite

Cabin in South Boston

5.0 out of 5 average rating, 6 reviews

Lakefront Cabin

26 Sep – 3 Oct

₹11,724 per night
Guest favourite

Home in Halifax

5.0 out of 5 average rating, 24 reviews

"The Guest House of Halifax"

13–20 Jan

₹11,397 per night
Guest favourite

Home in Halifax

5.0 out of 5 average rating, 21 reviews

The Lucky Leah - Charming Home in Downtown Halifax

19–26 Feb

₹16,819 per night
Guest favourite

Home in Clarksville

4.95 out of 5 average rating, 43 reviews

Country Living near Buggs Island/Kerr Lake

30 Dec – 6 Jan

₹9,764 per night
Guest favourite

Home in Roxboro

5.0 out of 5 average rating, 25 reviews

Long’s Lakehouse

16–23 Dec

₹12,102 per night
Guest favourite

Tiny home in Hillsborough

4.99 out of 5 average rating, 83 reviews

Cozy School Bus Getaway - 15 minutes to Duke!

19–24 May

₹9,867 per night
Guest favourite

Flat in South Boston

5.0 out of 5 average rating, 18 reviews

Quiet Downtown Loft

19–26 Feb

₹8,751 per night
Guest favourite

Flat in Clarksville

4.98 out of 5 average rating, 91 reviews

Cozy Getaway Efficiency on Buggs Island/Kerr Lake

25 Sep – 2 Oct

₹12,466 per night
Guest favourite

Flat in Clarksville

5.0 out of 5 average rating, 20 reviews

Gilliland Hotel 1898

21–28 Dec

₹10,261 per night
Guest favourite

Cabin in Roxboro

5.0 out of 5 average rating, 31 reviews

Moonlight Cabin - Lakefront Stay

1–8 May

₹18,949 per night

Quick stats about holiday 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

₹1,667 before taxes and fees

Destinations to explore

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