Holiday Rentals in South Boston

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Our top choices for South Boston holiday rentals

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 €315
includes taxes & fees
31 Dec - 1 Jan 2026
Boutique Guest Stay in Downtown Clarksville
10.0 out of 10, Exceptional, (4)
"This home was great for our short stay."
United States
Lauren M.
The price is €370
includes taxes & fees
31 Dec - 1 Jan 2026
Home featuring 3 Rooms 1 Bath Sleeps 6 Guest

Holiday 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.
The price is €378
includes taxes & fees
5 Jan - 6 Jan 2026
Walking Distance to Casino
10.0 out of 10, Exceptional, (1)
"Great unit, thoroughly enjoyed staying here."
United States
Joseph M.
The price is €199
includes taxes & fees
12 Jan - 13 Jan 2026
Insta-worthy 2Bd/1Ba Apt Steps from Downtown!
9.8 out of 10, Exceptional, (37)
"Perfect location to the casino and restaurants. We loved our stay. "
United States
Gail
The price is €226
includes taxes & fees
2 Jan - 3 Jan 2026
Located in Historic Old West End. Minutes from the River District and Casino.

Holiday Home in Danville

Cozy 3bedroom near Caesars Virginia
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 €247
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy 3bedroom near Caesars Virginia
The price is €235
includes taxes & fees
31 Dec - 1 Jan 2026
Chic Haven: 2b/1bath in the Heart of Danville
10.0 out of 10, Exceptional, (2)
"Perfect for a short family stay. Nice neighborhood."
United States
Shelly H.
The price is €319
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy 3 bdrm 2bath home close to Averrett University (smoking allowed)
2.0 star property
The price is €494
includes taxes & fees
4 Jan - 5 Jan 2026
Ranch-Style Retreat | 3BR/2BA | Central Location
10.0 out of 10, Exceptional, (10)
"We really enjoyed our stay!"
United States
Connie R.
Church of the Perpetual Boogie: near VIR & Casino
2.0 star property
The price is €451
includes taxes & fees
4 Jan - 5 Jan 2026
Walking Distance to Casino! Cozy stay in prime location!
9.0 out of 10, Wonderful, (7)
"The house was fantastic!"
United States
Chris L.
The price is €472
includes taxes & fees
31 Dec - 1 Jan 2026
Vacation home just 4 minutes drive to Caesars Virginia Casino
The price is €548
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious 4BR Retreat with salt water pool & hot tub
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 €712
includes taxes & fees
31 Dec - 1 Jan 2026
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.
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Top South Boston Hotel Reviews

Find out more about South Boston

Everything you need to know about South Boston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Boston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Boston holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Boston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Boston holiday rentals we have selected for you start as low as €226 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Boston rentals

At Expedia, we put the best South Boston holiday 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 holiday.

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 holiday rentals in South Boston?

Yes, there are holiday rentals in South Boston close to Vaughan St. Park, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that South Boston has to offer?

Located in Historic Old West End. Minutes from the River District and Casino.: This holiday home rental outside of South Boston is equipped with a BBQ, 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 holiday rentals are there in South Boston?

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

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 holiday rentals like in South Boston?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Boston. Holiday rentals feature amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.