Photo by kristy in VA

South Boston Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for South Boston vacation rentals

Boutique Guest Stay in Downtown Clarksville

Boutique Guest Stay in Downtown Clarksville
Clarksville
9.8 out of 10, Exceptional, (12)
"We enjoyed our stay! Very clean and easy check in and out. Great location. "
United States
Danielle N.
The price is ¥24,660
¥55,403 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Boutique Guest Stay in Downtown Clarksville

Home featuring 3 Rooms 1 Bath Sleeps 6 Guest

Home featuring 3 Rooms 1 Bath Sleeps 6 Guest
Roxboro
10.0 out of 10, Exceptional, (4)
"This home was great for our short stay."
United States
Lauren M.
The price is ¥26,069
¥66,818 total
includes taxes & fees
Dec 30 - Dec 31
Home featuring 3 Rooms 1 Bath Sleeps 6 Guest

Walking Distance to Casino

Walking Distance to Casino
Danvilel
10.0 out of 10, Exceptional, (27)
"It is a very nice little home with a well thought out layout. Check in and out were super smooth and the bed was very comfortable. Will stay again when we come to town. "
United States
Chris H.
The price is ¥18,491
¥67,001 total
includes taxes & fees
Dec 30 - Dec 31
Walking Distance to Casino

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

Insta-worthy 2Bd/1Ba Apt Steps from Downtown!
Danville
10.0 out of 10, Exceptional, (1)
"Great unit, thoroughly enjoyed staying here."
United States
Joseph M.
The price is ¥12,228
¥35,922 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Insta-worthy 2Bd/1Ba Apt Steps from Downtown!

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, (36)
"Perfect location to the casino and restaurants. We loved our stay. "
United States
Gail
The price is ¥19,023
¥40,825 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Located in Historic Old West End. Minutes from the River District and Casino.

Cozy 3bedroom near Caesars Virginia

Cozy 3bedroom near Caesars Virginia
Danville
10.0 out of 10, Exceptional, (1)
"Host very responsive to questions. Location for us was great, close to restaurants we go to and not a long ride to Martinsville Speedway."
United States
Susan D.
The price is ¥10,709
¥44,564 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Cozy 3bedroom near Caesars Virginia

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

Chic Haven: 2b/1bath in the Heart of Danville
Danville
The price is ¥17,567
¥43,276 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Chic Haven: 2b/1bath in the Heart of Danville

Cozy 3 bdrm 2bath home close to Averrett University (smoking allowed)

Cozy 3 bdrm 2bath home close to Averrett University (smoking allowed)
Danville
10.0 out of 10, Exceptional, (2)
"Perfect for a short family stay. Nice neighborhood."
United States
Shelly H.
The price is ¥31,314
¥58,095 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Cozy 3 bdrm 2bath home close to Averrett University (smoking allowed)

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

Ranch-Style Retreat | 3BR/2BA | Central Location
2.0 star property
Danville
The price is ¥26,175
¥83,948 total
includes taxes & fees
Dec 30 - Dec 31
Ranch-Style Retreat | 3BR/2BA | Central Location

Church of the Perpetual Boogie: near VIR & Casino

Church of the Perpetual Boogie: near VIR & Casino
Danville
10.0 out of 10, Exceptional, (10)
"We really enjoyed our stay!"
United States
Connie R.
The price is ¥53,758
¥98,423 total
includes taxes & fees
Dec 30 - Dec 31
Church of the Perpetual Boogie: near VIR & Casino

Walking Distance to Casino! Cozy stay in prime location!

Walking Distance to Casino! Cozy stay in prime location!
2.0 star property
Danville
The price is ¥24,425
¥81,360 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Walking Distance to Casino! Cozy stay in prime location!

Vacation home just 4 minutes drive to Caesars Virginia Casino

Vacation home just 4 minutes drive to Caesars Virginia Casino
Danville
9.0 out of 10, Wonderful, (7)
"The house was fantastic!"
United States
Chris L.
The price is ¥50,024
¥83,776 total
includes taxes & fees
Dec 30 - Dec 31
Vacation home just 4 minutes drive to Caesars Virginia Casino

Spacious 4BR Retreat with salt water pool & hot tub

Spacious 4BR Retreat with salt water pool & hot tub
Danville
Spacious 4BR Retreat with salt water pool & hot tub

Cozy home near golf & casino! in tranquil Danville

Cozy home near golf & casino! in tranquil Danville
Danville
6.0 out of 10, (2)
"The state there was excellent the property and every essential you can think of was fully loaded the only issue was the code process. We got locked out and it tried to reach property manager and could not so we reached out to BRBO and they contacted him but with no avail we were unsuccessful however we did manage to get into the"
United States
Linda H.
The price is ¥51,512
¥128,247 total
includes taxes & fees
Dec 30 - Dec 31
Cozy home near golf & casino! in tranquil 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.
Save an average of 15% on thousands of hotels when you're signed in

Top South Boston Hotel Reviews

Find out more about South Boston

Search for holiday rentals in South Boston on Expedia! You can easily find your home rentals, villas, holiday apartments in South Boston using one of the methods below:

  • View our selection of featured holiday rentals in South Boston
  • Use the map to find apartments and other holiday homes in the South Boston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Boston while they last

Look no further and take a look at our great range of rental properties in South Boston!

Frequently asked questions

Can I find vacation rentals in South Boston?

Yes, we give you a choice of vacation rentals in South Boston near Vaughan St. 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?

Located in Historic Old West End. Minutes from the River District and Casino.: This vacation home rental near South Boston is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

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 Vaughan St. Park and North Main Street 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.