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Top Holiday Rentals in South Boston

2 Mi to South Boston Speedway: Cozy Tiny Home!

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

Solar powered cottage at lake, with dock, on private 300 acre timber preserve

9.8 out of 10, Exceptional, (152)
"The property is amazing. This was my second time staying and it was even better than the first"
Solar powered cottage at lake, with dock, on private 300 acre timber preserve

Located in Historic Old West End. Minutes from the River District and Casino.

9.8 out of 10, Exceptional, (19)
"Had a wonderful Sister getaway weekend at the Vintage Charm! The home was perfect for our weekend, so clean and comfortable! Lovely neighborhood with lots to do in the area, we can’t wait to go back!!"
The price is £198
includes taxes & fees
26 Jun - 27 Jun
Located in Historic Old West End. Minutes from the River District and Casino.

WATERFRONT LOG HOME! HOT TUB/2 FIREPLACES/FIRE PIT/LARGE DECK/77" TV SUR. SOUND!

9.6 out of 10, Exceptional, (65)
"Excellent place to relax and connect. Cozy home with plenty of space for 4 guys. Loved the fire pit and the big screen to watch the World Series. Definitely would return especially with proximity to Biggs Island Brewery!"
WATERFRONT LOG HOME! HOT TUB/2 FIREPLACES/FIRE PIT/LARGE DECK/77" TV SUR. SOUND!

Single-Story Cabin on Hyco Lake: Swim & Unwind!

8.4 out of 10, Very good, (5)
"Had a great time!!!!! I highly recommend the cabin!!!!!"
Single-Story Cabin on Hyco Lake: Swim & Unwind!

Walking Distance to Casino. No cleaning fee.

10.0 out of 10, Exceptional, (17)
"This home was great, very clean and well stocked."
Walking Distance to Casino. No cleaning fee.

Historic 2 br & 1 ba On the River

9.8 out of 10, Exceptional, (40)
"We enjoyed our stay, very clean and comfortable. Good food near by and things to do within walking distance. Thank you"
Historic 2 br & 1 ba On the River

Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

10.0 out of 10, Exceptional, (90)
"We enjoyed our stay and loved the cabin."
Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly

9.6 out of 10, Exceptional, (87)
"Very accommodating house, great spot on the lake"
Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly

Charming 4-bedroom 3-bath house on beautiful Hyco Lake with boat dock.

2.0 star property
10.0 out of 10, Exceptional, (12)
"Love the lake-easy walk, great dock, great accommodations"
Charming 4-bedroom 3-bath house on beautiful Hyco Lake with boat dock.

Kerr Lake waterfront home w/dock, just off main channel, close to town!

2.0 star property
10.0 out of 10, Exceptional, (3)
"We really enjoyed the lake house. Loved the location. Host was great! Hope to come back soon!! "
Kerr Lake waterfront home w/dock, just off main channel, close to town!

Cozy Lakefront Cabin in Semora w/ Large Dock!

9.8 out of 10, Exceptional, (6)
"Awesome location"
Cozy Lakefront Cabin in Semora w/ Large Dock!

Coleman 202 RD travel trailer. Located on the owner's lakefront property!

2.0 star property
10.0 out of 10, Exceptional, (1)
"We enjoyed or stay! The camper was perfect for the weekend. Hunter and his family were very nice and accommodating. The camper was well stocked and really clean. "
The price is £153
includes taxes & fees
29 Jun - 30 Jun
Coleman 202 RD travel trailer. Located on the owner's lakefront property!

Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach

10.0 out of 10, Exceptional, (178)
"Such a relaxing weekend. Great bird watching. Fire pit was great. Looking forward to visiting again. Owners were very accommodating. We will definitely visit again."
Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach

Cute Lakefront Cottage

9.8 out of 10, Exceptional, (50)
"Loved how simple is was."
Cute Lakefront Cottage

Miles to VIR, Caesar's VA Casino, Martinsv'l , S.Boston, Priv. Pool POOLS OPEN

10.0 out of 10, Exceptional, (31)
"Always a joy to stay here! We look forward to coming back again some day soon!"
Miles to VIR, Caesar's VA Casino, Martinsv'l , S.Boston, Priv. Pool POOLS OPEN

Vacation home just 4 minutes drive to Caesars Virginia Casino

10.0 out of 10, Exceptional, (3)
"Perfect house to get a night out at the casino."
The price is £220
includes taxes & fees
26 Jun - 27 Jun
Vacation home just 4 minutes drive to Caesars Virginia 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. "
The price is £133
includes taxes & fees
1 Jul - 2 Jul
Log Cabin Retreat/Pet Friendly: Lake, Golf & Wine

Cozy cabin w/ hot tub! Lake access w/ walk to pier

9.8 out of 10, Exceptional, (9)
"Beautiful home, enjoyed our family time together!"
Cozy cabin w/ hot tub! Lake access w/ walk to pier

6 Bedrooms, Lakefront, Hot-Tub & Private Dock

9.0 out of 10, Wonderful, (14)
"Loved every part of our stay. Home is in a beautiful quiet area and the house was very nice. "
6 Bedrooms, Lakefront, Hot-Tub & Private Dock
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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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 FIREPLACES/FIRE PIT/LARGE DECK/77" TV SUR. SOUND!: 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 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.