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Holiday Rentals in South Boston

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Our top choices for South Boston holiday rentals

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
10.0 out of 10, Exceptional, (51 reviews)
"This was an amazing one night getaway for our anniversary, and I truly enjoyed myself. The house was very cozy, comfortable and clean. I would definitely stay here again."
United States
Lester A.
The price is €255
includes taxes & fees
1 Jul - 2 Jul
Located in Historic Old West End. Minutes from the River District and Casino.

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 €418
includes taxes & fees
1 Jul - 2 Jul
Walking Distance to Casino

Historic Court Square Apt

Historic Court Square Apt
Roxboro
9.6 out of 10, Exceptional, (5 reviews)
"We stayed here for 2 weeks and loved it. Great location"
United States
BRAD M.
Historic Court Square Apt

Lakefront with Million Dollar Views on HYCO Lake

Lakefront with Million Dollar Views on HYCO Lake
Leasburg
10.0 out of 10, Exceptional, (13 reviews)
"Our family greatly enjoyed our stay! The home was lovely - just as pictured. The whole house was fully equipped with many items visitors may need/want at a rental. Communication with the owner was super easy - always accessible and very prompt to get back to me. Highly recommend this VRBO "
United States
Kim S.
The price is €495
includes taxes & fees
15 Jul - 16 Jul
Lakefront with Million Dollar Views on HYCO Lake

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

Insta-worthy 2Bd/1Ba Apt | Minutes from Downtown!
Danville
10.0 out of 10, Exceptional, (4 reviews)
"Great unit, thoroughly enjoyed staying here."
United States
Joseph M.
The price is €259
includes taxes & fees
27 Jul - 28 Jul
Insta-worthy 2Bd/1Ba Apt | Minutes from Downtown!

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 €660
includes taxes & fees
7 Jul - 8 Jul
Lakefront Retreat with Hot Tub + Fire Pit + Water Views at Hyco Lake

Homestead on Hyco - 21 Min to VIR

Homestead on Hyco - 21 Min to VIR
Semora
10.0 out of 10, Exceptional, (1 review)
"We had a very comfortable stay while working at VIR. The location was a great spot to unwind after a long day at the track! Thank you for having us! We hope to stay again. "
United States
Hilary G.
Homestead on Hyco - 21 Min to VIR

Iconic Church Turned Unique Stay (Casino/VIR)

Iconic Church Turned Unique Stay (Casino/VIR)
Danville
10.0 out of 10, Exceptional, (10 reviews)
"We really enjoyed our stay!"
United States
Connie R.
The price is €669
includes taxes & fees
9 Jul - 10 Jul
Iconic Church Turned Unique Stay (Casino/VIR)

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 €470
includes taxes & fees
1 Jul - 2 Jul
Walk to Caesars Casino | 3BR Home w/King Bed

Checkmate! Your Winning Lake Escape! Near VIR, Caesar's Casino, Unsalted Farm

Checkmate! Your Winning Lake Escape! Near VIR, Caesar's Casino, Unsalted Farm
Semora
10.0 out of 10, Exceptional, (1 review)
"great"
United States
Scott B.
Checkmate! Your Winning Lake Escape! Near VIR, Caesar's Casino, Unsalted Farm

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

Our Point of View on Hyco Lake

Our Point of View on Hyco Lake
Semora
Our Point of View on Hyco Lake
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 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 North Main Street 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?

WATERFRONT LOG HOME/HOT TUB/2 FIREPLACE/77" TV/STARLINK/ LG DECK/FIRE PIT: This holiday home rental outside of South Boston is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with 1 hot tub and a selection of books.

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 North Main Street Park and Vaughan St. Park, whereas Tobacco Heritage Trail - Cotton Mill Park Trailhead, South Boston and Hudson Heritage Farms 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.