South Boston Vacation Rentals

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Our top choices for South Boston vacation rentals

Remodeled historic cottage with 2master suites. 8 mile bike trail.

Remodeled historic cottage with 2master suites. 8 mile bike trail.
South Boston
$239 nightly
The price is $267
Feb 11 - Feb 12
Total with taxes and fees
Remodeled historic cottage with 2master suites. 8 mile bike trail.

Boutique Guest Stay in Downtown Clarksville

Boutique Guest Stay in Downtown Clarksville
Clarksville
9.8 out of 10, Exceptional, (12 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.
$270 nightly
The price is $301
Jan 31 - Feb 1
Total with taxes and fees
Boutique Guest Stay in Downtown Clarksville

Driftwood Cove Cottage - 2mi from lake

Driftwood Cove Cottage - 2mi from lake
Buffalo Junction
$122 nightly
The price is $135
Jan 31 - Feb 1
Total with taxes and fees
Driftwood Cove Cottage - 2mi from lake

Walking Distance to Casino

Walking Distance to Casino
Danvilel
10.0 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay at this well stocked home. Bed was comfortable, good coffee. Close to the new Ceasar’s where we dropped some !"
United States
Joanie F.
$437 nightly
The price is $502
Feb 2 - Feb 3
Total with taxes and fees
Walking Distance to Casino

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, (38 reviews)
"Perfect location to the casino and restaurants. We loved our stay. "
United States
Gail
$227 nightly
The price is $262
Jan 31 - Feb 1
Total with taxes and fees
Located in Historic Old West End. Minutes from the River District and Casino.

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.
$219 nightly
The price is $253
Feb 1 - Feb 2
Total with taxes and fees
Insta-worthy 2Bd/1Ba Apt Steps from Downtown!

Cozy 3bedroom near Caesars Virginia

Cozy 3bedroom near Caesars Virginia
Danville
7.6 out of 10, Good, (4 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.
$215 nightly
The price is $248
Feb 1 - Feb 2
Total with taxes and fees
Cozy 3bedroom near Caesars Virginia

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 reviews)
"This home was great for our short stay."
United States
Lauren M.
$386 nightly
The price is $435
Jan 30 - Jan 31
Total with taxes and fees
Home featuring 3 Rooms 1 Bath Sleeps 6 Guest

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.
$403 nightly
The price is $464
Feb 8 - Feb 9
Total with taxes and fees
Cozy midtown 3 bedroom/1 bath

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 reviews)
"Perfect for a short family stay. Nice neighborhood."
United States
Shelly H.
$324 nightly
The price is $373
Jan 30 - Jan 31
Total with taxes and fees
Cozy 3 bdrm 2bath home close to Averrett University (smoking allowed)

Walking Distance to Casino! Cozy stay in prime location!

Walking Distance to Casino! Cozy stay in prime location!
Danville
$452 nightly
The price is $520
Feb 1 - Feb 2
Total with taxes and fees
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 reviews)
"The house was fantastic!"
United States
Chris L.
$294 nightly
The price is $340
Mar 1 - Mar 2
Total with taxes and fees
Vacation home just 4 minutes drive to Caesars Virginia Casino

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

Ranch-Style Retreat | 3BR/2BA | Central Location
Danville
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 reviews)
"We really enjoyed our stay!"
United States
Connie R.
$483 nightly
The price is $554
Mar 1 - Mar 2
Total with taxes and fees
Church of the Perpetual Boogie: near VIR & 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
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 $248 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?

The Cedar Farm Close To VIR, Danville: This vacation home rental near South Boston is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 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 4 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.