South Boston Vacation Rentals

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Our top choices for South Boston vacation rentals

Charming remodeled historic home in the small town of South Boston, Virginia.

Charming remodeled historic home in the small town of South Boston, Virginia.
South Boston
10.0 out of 10, Exceptional, (6 reviews)
"The property was not available, but the owner took great care of us and made sure that we had everything we needed. The owner was great and we were well pleased. "
United States
Ricky L.
The price is CA $247
CA $521 total
includes taxes & fees
May 11 - May 12
Charming remodeled historic home in the small town of South Boston, Virginia.

Located in Historic Old West End. Minutes from the River District and Casino.

Located in Historic Old West End. Minutes from the River District and Casino.
Danville
9.8 out of 10, Exceptional, (46 reviews)
"Perfect location to the casino and restaurants. We loved our stay. "
United States
Gail
The price is CA $221
CA $435 total
includes taxes & fees
May 20 - May 21
Located in Historic Old West End. Minutes from the River District and Casino.

Lakefront Retreat with Hot Tub + Fire Pit + Water Views at Hyco Lake

Lakefront Retreat with Hot Tub + Fire Pit + Water Views at Hyco Lake
Semora
10.0 out of 10, Exceptional, (1 review)
"The views, the serenity and quietness of the area, the simplicity of the home, and the amenities like hottub and firepit all stood out. The yard is very beautifully landscaped and maintained. The ease of access right off a main road was nice too, as we did venture to explore other areas which were off the beaten path on lengthy gravel roads. The host was extremely welcoming and accessible if needed though we did not require anything. It was a great place to reset after the busy holiday...
United States
Wendy A.
The price is CA $451
CA $875 total
includes taxes & fees
May 12 - May 13
Lakefront Retreat with Hot Tub + Fire Pit + Water Views at Hyco Lake

Walking Distance to Casino

Walking Distance to Casino
Danvilel
10.0 out of 10, Exceptional, (28 reviews)
"Room where great, loved the mattress. Definitely had a great night sleep here!"
United States
Brenda
The price is CA $196
CA $655 total
includes taxes & fees
May 20 - May 21
Walking Distance to Casino

Church of the Perpetual Boogie: near VIR & Casino

Church of the Perpetual Boogie: near VIR & Casino
Danville
10.0 out of 10, Exceptional, (10 reviews)
"We really enjoyed our stay!"
United States
Connie R.
The price is CA $313
CA $680 total
includes taxes & fees
May 12 - May 13
Church of the Perpetual Boogie: near VIR & Casino

Charming 4-bedroom 3-bath house on beautiful Hyco Lake with boat dock.

Charming 4-bedroom 3-bath house on beautiful Hyco Lake with boat dock.
Semora
10.0 out of 10, Exceptional, (25 reviews)
"Great quiet location with scenic lake view"
United States
Keith R.
The price is CA $307
CA $564 total
includes taxes & fees
May 20 - May 21
Charming 4-bedroom 3-bath house on beautiful Hyco Lake with boat dock.

Buggs Island/Kerr Lake Water Views, Shared Dock

Buggs Island/Kerr Lake Water Views, Shared Dock
Clarksville
10.0 out of 10, Exceptional, (17 reviews)
"The house was perfect for our week vacation. Clean and nicely decorated, we had everything we needed.Our hosts were very responsive and pleasant. The home is in a great location with large dock.Will definitely stay again when we are in Clarksville."
United States
Tiffany W.
The price is CA $264
CA $683 total
includes taxes & fees
May 11 - May 12
Buggs Island/Kerr Lake Water Views, Shared Dock

Boutique Guest Stay in Downtown Clarksville

Boutique Guest Stay in Downtown Clarksville
Clarksville
9.8 out of 10, Exceptional, (14 reviews)
"Our weekend getaway was perfect, thanks to our stay at this cute apartment. Our host was super quick to respond and kept us informed of everything we needed to know. The decor was adorable and the location was the ideal spot to walk to everything you need. The town was quiet and friendly and a great place for a relaxing visit. "
United States
David J.
The price is CA $289
CA $586 total
includes taxes & fees
May 20 - May 21
Boutique Guest Stay in Downtown Clarksville

10 minutes from VIR. Great bass fishing! Rustic cottage on large private pond.

10 minutes from VIR. Great bass fishing! Rustic cottage on large private pond.
Alton
10.0 out of 10, Exceptional, (1 review)
"We came down for an event at VIR. The hosts were fantastic and the home was lovely. Will be back!"
United States
Chris N.
The price is CA $615
CA $1,026 total
includes taxes & fees
May 14 - May 15
10 minutes from VIR. Great bass fishing! Rustic cottage on large private pond.

Insta-worthy 2Bd/1Ba Apt Steps from Downtown!

Insta-worthy 2Bd/1Ba Apt Steps from Downtown!
Danville
10.0 out of 10, Exceptional, (3 reviews)
"Great unit, thoroughly enjoyed staying here."
United States
Joseph M.
The price is CA $139
CA $361 total
includes taxes & fees
Jun 1 - Jun 2
Insta-worthy 2Bd/1Ba Apt Steps from Downtown!

Cozy midtown 3 bedroom/1 bath

Cozy midtown 3 bedroom/1 bath
Danville
10.0 out of 10, Exceptional, (2 reviews)
"Great stay! Misty was very welcoming. Will definitely visit again!"
United States
Hope B.
The price is CA $162
CA $638 total
includes taxes & fees
May 10 - May 11
Cozy midtown 3 bedroom/1 bath

Walk to Caesars Casino | 3BR Home w/King Bed

Walk to Caesars Casino | 3BR Home w/King Bed
Danville
10.0 out of 10, Exceptional, (1 review)
"Great stay! We spent most of the time at Caesar's Casino, but the house served our purposes perfectly. The single bathroom is a drag, but then again, we didn't need to use it much. Price is fair considering Casino prices, but a little steep for the location. "
United States
Robert B.
The price is CA $233
CA $751 total
includes taxes & fees
May 11 - May 12
Walk to Caesars Casino | 3BR Home w/King Bed

Cozy 3bedroom near Caesars Virginia

Cozy 3bedroom near Caesars Virginia
Danville
8.0 out of 10, Very good, (8 reviews)
"We booked this house to go to the Casino. It was perfect. Less than a 5 minute drive. House was clean, warm and comfortable. "
United States
Evelyn K.
The price is CA $111
CA $415 total
includes taxes & fees
May 10 - May 11
Cozy 3bedroom near Caesars Virginia

Ranch-Style Retreat | 3BR/2BA | Central Location

Ranch-Style Retreat | 3BR/2BA | Central Location
Danville
The price is CA $282
CA $852 total
includes taxes & fees
May 31 - Jun 1
Ranch-Style Retreat | 3BR/2BA | Central Location

Chic Haven: 2b/1bath in the Heart of Danville

Chic Haven: 2b/1bath in the Heart of Danville
Danville
The price is CA $139
CA $361 total
includes taxes & fees
Jun 1 - Jun 2
Chic Haven: 2b/1bath in the Heart of Danville
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Boston Hotel Reviews

Find out more about South Boston

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with South Boston. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in South Boston?

Yes, we give you a choice of vacation rentals in South Boston near North Main Street Park, or you can select a more remote option if you want a relaxing stay. Our travelers say South Boston has a good selection of restaurants. Make sure you have time to check out the local tours and entertainment choices during your trip.

What are some of the best vacation rentals that South Boston has to offer?

Charming 4-bedroom 3-bath house on beautiful Hyco Lake with boat dock. : This vacation home rental near South Boston offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in South Boston?

Choose from 3 Expedia vacation rentals in South Boston for a memorable vacation.

What can I see and do in South Boston?

Family-friendly attractions include North Main Street Park and Vaughan St. Park, whereas Hudson Heritage Farms and Constitution Square are a couple of great spots to enjoy the outdoors. Downtown South Boston Farmers Market and South Boston Speedway are other places to visit while you're in town.

What are vacation rentals like in South Boston?

Vacation rentals are privately owned properties you can reserve for a short or long stay in South Boston. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for small groups.