Photo by kristy in VA

South Boston Vacation Rentals

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Our top choices for South Boston vacation rentals

3.0 star property
2 Mi to South Boston Speedway: Cozy Tiny Home!

Apartment in South Boston

Studio 2 Mi to South Boston Speedway
3.0 star property
Studio 2 Mi to South Boston Speedway
9.8 out of 10, Exceptional, (35)
"Perfect location to the casino and restaurants. We loved our stay. "
United States
Gail
$229 nightly
The price is $264
Dec 22 - Dec 23
Total with taxes and fees
Located in Historic Old West End. Minutes from the River District and Casino.
9.6 out of 10, Exceptional, (35)
"Beautiful property and owners were very prompt and responsive."
United States
Loralee S.
Bring YOUR BOAT- Private Dock, Deep Water, Gameroom and Firepit

Vacation Home in Danvilel

Walking Distance to Casino
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.
$377 nightly
The price is $434
Dec 17 - Dec 18
Total with taxes and fees
Walking Distance to Casino
10.0 out of 10, Exceptional, (100)
"secluded lakeside property, within walking distance to the town center. my family enjoyed the many amenities and we plan on returning next year"
United States
James m.
Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA
9.8 out of 10, Exceptional, (96)
"My family rented this for an Easter weekend. The owner was very accommodating and they had a great time!! "
United States
Quynh R.
H2O-FRONT Chef’s_Kitchen Gig-WiFi DogsOK EV-Charger Alexa
9.2 out of 10, Wonderful, (10)
"Super fun and very comfortable! Would definitely stay here again!"
United States
Robert L.
Charming 1915 Heritage Home: Historic Renovation, Modern Flair, Central Location
9.6 out of 10, Exceptional, (15)
"Great Lake stay for a weekend!"
United States
Beth G.
Exquisite property on the main channel- Buggs Island/ Kerr Lake waterfront home!

Vacation Home in Ringgold

The Cedar Farm Close To VIR, Danville
10.0 out of 10, Exceptional, (37)
"Very nice property quiet and beautiful area. House was clean and had many amenities. Would recommend and drive to VIR was fun from there also"
United States
Brian C.
The Cedar Farm Close To VIR, Danville
8.4 out of 10, Very Good, (9)
"We had a lovely stay at this historic mansion. It's very spacious and nicely located. We had no issues."
United States
Sean C.
Mansion on Main | Danville Vacation Rental
9.6 out of 10, Exceptional, (72)
"Would definitely stay again! "
United States
Chelsea K.
WATERFRONT LOG HOME FOR FAMILY CHRISTMAS! HOT TUB/FIREPLACES/LARGE DECK/FIRE PIT
9.6 out of 10, Exceptional, (19)
"Absolutely amazing "
United States
Kris P.
Kerr Contentment Kerr Lake/Buggs Island waterfront, an amazing view
9.6 out of 10, Exceptional, (95)
"Was perfect place for us "
United States
jc t.
Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly
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.
$677 nightly
The price is $777
Dec 18 - Dec 19
Total with taxes and fees
Cozy home near golf & casino! in tranquil Danville
9.0 out of 10, Wonderful, (7)
"The house was fantastic!"
United States
Chris L.
$473 nightly
The price is $543
Dec 17 - Dec 18
Total with taxes and fees
Vacation home just 4 minutes drive to Caesars Virginia Casino
10.0 out of 10, Exceptional, (14)
"The cabin was exactly as advertised and we all felt right at home the minute we walked in. We had everything we needed and thoroughly enjoyed our stay. We would definitely rent this cabin again."
United States
Tanya S.
Cozy cabin w/ hot tub! Lake access w/ walk to pier
10.0 out of 10, Exceptional, (16)
"This place is lovely. It was clean, comfortable, plenty of parking, pet friendly, great amenities. The owner was responsive and friendly. Hope to return again in the future!!!"
United States
Debra R.
Charming 4-bedroom 3-bath house on beautiful Hyco Lake with boat dock.

Vacation Home in Danville

Spacious 3bd/2ba near Casino
9.4 out of 10, Exceptional, (3)
"The host was very timely. Location was close to venues. "
United States
Amie S.
Spacious 3bd/2ba near Casino

Vacation Home in Danville

Welcoming 3bd/2ba near Averett
10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay. This is a nice neighborhood, calm quiet. There is not much traffic on these streets, good for walking and if you are athletic or like a challenge, good for running hills! To me the rooms were more spacious than what they appear in the pictures. I love houses of this age and style, it has so much character.The host was easy to reach, if needed (although I did not need anything).There were spices, salt and pepper along with Saran Wrap, wax paper, etc, all the kitchen...
United States
Lil N.
Welcoming 3bd/2ba near Averett
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

Everything you need to know about South Boston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Boston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Boston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Boston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Boston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Boston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $264 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Boston rentals

At Expedia, we put the best South Boston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Boston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Boston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Boston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

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 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. South Boston Speedway and South Boston Town Hall 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.