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South Boston Holiday Rentals

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Holiday Rentals in South Boston

Peaceful RV site Full Hookup on 175acre Farm
10.0 out of 10, Exceptional, (2)
"Stayed here in a 40’ rv trailer for the Rock Fest. Stephanie was super helpful. Nice quiet property with plenty of room to spread out."
United States
Michael G.
The price is NZ$136
includes taxes & fees
29 Oct - 30 Oct
Peaceful RV site Full Hookup on 175acre Farm
Walking Distance to Casino
10.0 out of 10, Exceptional, (25)
"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 NZ$789
includes taxes & fees
27 Oct - 28 Oct
Walking Distance to Casino
Log Cabin Retreat/Pet Friendly: Lake, Golf & Wine
2.0 star property
10.0 out of 10, Exceptional, (5)
"Great getaway place for couples or small families. "
United States
Tom H.
The price is NZ$307
includes taxes & fees
27 Oct - 28 Oct
Log Cabin Retreat/Pet Friendly: Lake, Golf & Wine
Insta-worthy 2Bd/1Ba Apt Steps from Downtown!
10.0 out of 10, Exceptional, (1)
"Great unit, thoroughly enjoyed staying here."
United States
Joseph M.
The price is NZ$505
includes taxes & fees
5 Nov - 6 Nov
Insta-worthy 2Bd/1Ba Apt Steps from Downtown!
Located in Historic Old West End. Minutes from the River District and Casino.
9.8 out of 10, Exceptional, (32)
"Perfect location to the casino and restaurants. We loved our stay. "
United States
Gail
The price is NZ$456
includes taxes & fees
27 Oct - 28 Oct
Located in Historic Old West End. Minutes from the River District and Casino.
Home featuring 3 Rooms 1 Bath Sleeps 6 Guest
10.0 out of 10, Exceptional, (4)
"This home was great for our short stay."
United States
Lauren M.
The price is NZ$287
includes taxes & fees
3 Nov - 4 Nov
Home featuring 3 Rooms 1 Bath Sleeps 6 Guest
Boutique Guest Stay in Downtown Clarksville
9.8 out of 10, Exceptional, (12)
"This was our second stay at this property and we thoroughly enjoyed it again!The property is clean, and the communication with the host was excellent. The people of Clarksville are so kind and welcoming. The location is great for lake activities, or exploring the area. We found some great local breweries and vinyards within reasonable distance and of course enjoyed Buggs Island Brewery for live music lakeside in the evenings. Highly recommend!!"
United States
Heather C.
The price is NZ$626
includes taxes & fees
26 Oct - 27 Oct
Boutique Guest Stay in Downtown Clarksville
Vacation home just 4 minutes drive to Caesars Virginia Casino
10.0 out of 10, Exceptional, (6)
"The home was perfect for our family. I have stayed at several VRBO’s and this one has been the easiest entry by far. I will definitely book this home again for our events at VIR. "
United States
DEBRA K.
The price is NZ$565
includes taxes & fees
30 Oct - 31 Oct
Vacation home just 4 minutes drive to Caesars Virginia Casino
Chic Haven: 2b/1bath in the Heart of Danville
The price is NZ$509
includes taxes & fees
16 Nov - 17 Nov
Chic Haven: 2b/1bath in the Heart of Danville
Cozy 3 bdrm 2bath home close to Averrett University (smoking allowed)
10.0 out of 10, Exceptional, (2)
"We booked this house to attend what turned out to be a horrible festival called blueridge rock festival. While our festival had issues our rental did not! Our rental had plenty of space for us to invite friends over , bake a lasagna and play some card games together which helped salvage our trip. The home was very spacious, had a lot of nice touches such as a variety of Board games, extra dishes and cookware ect. Rooms were clean and beds were comfy! 10/10 would recommend."
United States
jasmine d.
The price is NZ$646
includes taxes & fees
29 Oct - 30 Oct
Cozy 3 bdrm 2bath home close to Averrett University (smoking allowed)
10 minutes from VIR. Great bass fishing! Rustic cottage on large private pond.
10.0 out of 10, Exceptional, (1)
"We came down for an event at VIR. The hosts were fantastic and the home was lovely. Will be back!"
United States
Chris N.
The price is NZ$968
includes taxes & fees
29 Oct - 30 Oct
10 minutes from VIR. Great bass fishing! Rustic cottage on large private pond.
Ranch-Style Retreat | 3BR/2BA | Central Location
2.0 star property
The price is NZ$958
includes taxes & fees
26 Oct - 27 Oct
Ranch-Style Retreat | 3BR/2BA | Central Location
Walking Distance to Casino! Cozy stay in prime location!
2.0 star property
The price is NZ$916
includes taxes & fees
27 Oct - 28 Oct
Walking Distance to Casino! Cozy stay in prime location!
Charming 4-bedroom 3-bath house on beautiful Hyco Lake with boat dock.
2.0 star property
10.0 out of 10, Exceptional, (15)
"Love the lake-easy walk, great dock, great accommodations"
United States
Lynn H.
The price is NZ$786
includes taxes & fees
2 Nov - 3 Nov
Charming 4-bedroom 3-bath house on beautiful Hyco Lake with boat dock.
Mayo Lake Getaway
10.0 out of 10, Exceptional, (1)
"Very nice home, clearly updated and super clean. All the amenities you could want (wifi, Keurig, Smart TV, updated baths, etc.) and just steps to the lake. Very secluded and quiet - we could see SO many stars each night. Lots to love about the place. Definitely recommend. "
United States
Bill D.
The price is NZ$768
includes taxes & fees
31 Oct - 1 Nov
Mayo Lake Getaway
Spacious 4BR Retreat w Pool
The price is NZ$1,266
includes taxes & fees
27 Oct - 28 Oct
Spacious 4BR Retreat w Pool
Church of the Perpetual Boogie: near VIR & Casino
10.0 out of 10, Exceptional, (10)
"We really enjoyed our stay!"
United States
Connie R.
The price is NZ$1,081
includes taxes & fees
28 Oct - 29 Oct
Church of the Perpetual Boogie: near VIR & Casino
Cozy home near golf & casino! in tranquil 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 NZ$1,868
includes taxes & fees
27 Oct - 28 Oct
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, 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 NZ$307 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?

Kerr/Buggs Island Lake waterfront home w/dock, just off main channel!: This holiday home rental outside of South Boston is located on a lake, and has a fireplace, a balcony and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.