
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.
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Popular amenities for South Boston holiday rentals
Other great holiday rentals in South Boston
Top guest favourite

Farm stay in Long Island
5 out of 5 average rating, 47 reviewsFarm Glamping 1 room cabin sleeps 4
RobertRating, 5 stars2 months ago
The farm is a great place to visit, especially for kids. It's a quiet and beautiful area with an absolutely wonderful family running the farm. Sheila and James were extremely hospitable and welcoming. The animals, from dogs to goats to sheep are numerous and fun to watch and be around. I can't wait to go back!
Top guest favourite

Home in Clarksville
4.97 out of 5 average rating, 67 reviewsCountry Living near Buggs Island/Kerr Lake
WendyRating, 5 stars3 weeks ago
We love it here. We have stayed twice before and is always our first choice when coming into town.
Guest favourite

Home in Leasburg
5 out of 5 average rating, 19 reviewsNew Listing! - Lakefront Cottage
RyanRating, 5 stars4 weeks ago
We had an amazing stay by the lake! The location was absolutely perfect—peaceful, scenic, and relaxing. The house was clean, cozy, and had everything we needed for a comfortable stay. Our host was responsive, accommodating, and made check-in seamless. We highly recommend this spot and can't wait to return!
Superhost

Tent in Henderson
5 out of 5 average rating, 3 reviewsNature Immersed Glamping Tent — "The Haven"
Tammy KingRating, 5 stars3 weeks ago
If you’re looking for a quiet, private and super comfy stay somewhere to enjoy the outdoors, then this is the place. Becky and Jim have a beautiful place. I stayed one night and couldn’t have been happier with my experience. Having the golf carts provides really easy access to the entire area, although we walked quite a bit just to enjoy the weather and really take in how gorgeous this place was. The community area was very well maintained, the bathrooms/showers were spotless 10/10 for cleanliness which is important to us. I loved the decor, and even the bull shaped Grill.. (you have to see it in person). The tent was very well put together. I felt very comfortable and at home while not loosing that woodsy feel. I loved falling asleep to the sounds of the outdoors. I highly recommend a stay with Becky and Jim. They were exceptional hosts. I will be back.
Guest favourite

Cycladic home in Buffalo Junction
5 out of 5 average rating, 5 reviewsThe Silo at Lake Front Winery
DavidRating, 5 stars1 week ago
The fact that you get to stay on location of this beautiful winery says it all !!! Ashley was not only a great host at the winery for the tastings she was a great host for the Silo as well !!! Don’t miss out on this stay it is one of a kind!!! Comfortable, cozy, and a silo to make it unique. I look forward to staying in the future when I am in town.

Home in Danville
5 out of 5 average rating, 3 reviewsThe Owl House
JerridRating, 5 stars3 weeks ago
Very quiet little neighborhood, but not too far away from the local restaurants. Plenty of space in the home. The enclosed back porch is a very nice seating area for a relaxing evening.
Guest favourite

Farm stay in Meherrin
4.97 out of 5 average rating, 33 reviewsScandinavian Tiny Home on Farm!
HaleyRating, 5 stars1 week ago
We really enjoyed the tucked away location and the simplicity of this tiny home. It had everything we needed for a quick, peaceful getaway! Matt was very responsive, we would definitely return!
Top guest favourite

Flat in Hurt
5 out of 5 average rating, 27 reviewsRoark Mill Retreat
ShyamalaRating, 5 stars2 weeks ago
This little apartment is actually a lot nicer than the photos suggest. Situated in a quiet neighborhood in the countryside, clean, cozy, and comfortable. Brianna is a great host, very responsive and welcoming. We really enjoyed our stay.
Quick stats about holiday rentals in South Boston
Total rentals
10 properties
Nightly prices starting at
₹2,603 before taxes and fees
Total number of reviews
200 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
Popular amenities
Gym, BBQ grill and Laptop-friendly workspace
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