Photo by kristy in VA

South Boston Holiday Rentals

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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!

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

9.6 out of 10, Exceptional, (20)
"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 NZ$437
includes taxes & fees
13 July - 14 July
Located in Historic Old West End. Minutes from the River District and Casino.

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

9.6 out of 10, Exceptional, (153)
"This is an amazing little cabin. Perfect for a couples getaway. We really enjoyed our stay. Very private!!!"
Solar powered cottage at lake, with dock, on private 300 acre timber preserve

Cute Lakefront Cottage

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

Walking Distance to Casino. No cleaning fee.

10.0 out of 10, Exceptional, (19)
"This home was great, very clean and well stocked."
Walking Distance to Casino. No cleaning fee.

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

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

2.0 star property
10.0 out of 10, Exceptional, (4)
"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!

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

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!

Backwoods Milton House 3BR&2bath 3 Miles from VIR

2.0 star property
9.6 out of 10, Exceptional, (10)
"Loved the location and the house was cute and furnished nicely."
Backwoods Milton House 3BR&2bath 3 Miles from VIR

Hidden Haven - Hot Tub, Outdoor Shower & Firepit

9.6 out of 10, Exceptional, (18)
"Staying here in the off-season was perfection! Surrounded by beautiful trees, the lake, wildlife, and quiet was so relaxing!"
Hidden Haven - Hot Tub, Outdoor Shower & Firepit

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

10.0 out of 10, Exceptional, (179)
"Great accommodations!"
Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach

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 NZ$354
includes taxes & fees
14 July - 15 July
Coleman 202 RD travel trailer. Located on the owner's lakefront property!

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

The Cedar Farm Close To VIR, Danville

10.0 out of 10, Exceptional, (33)
"Our stay was wonderful! The property was as described—clean, comfortable, and well-equipped with everything we needed. The host was responsive and made the check-in process seamless. The location was great, and we had a pleasant and relaxing experience. Would definitely stay again!"
The Cedar Farm Close To VIR, Danville

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

Renovated 1BR - 3 Block Walk to Casino - Clean, Quiet, Safe & Guest-Favorite

10.0 out of 10, Exceptional, (2)
"The space was a perfect size, with plenty of room for 3 people. The bathroom was incredible, and the Charles was very helpful and kind when we had questions. "
Renovated 1BR - 3 Block Walk to Casino - Clean, Quiet, Safe & Guest-Favorite

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 NZ$487
includes taxes & fees
14 July - 15 July
Vacation home just 4 minutes drive to Caesars Virginia Casino

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!

LAKE VIEW! FISHERMANS DREAM! CLOSE TO BLUESTONE BOAT LANDING!

9.8 out of 10, Exceptional, (9)
"Very nice place very clean and good if you have a boat also"
LAKE VIEW! FISHERMANS DREAM! CLOSE TO BLUESTONE BOAT LANDING!
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?

Located in Historic Old West End. Minutes from the River District and Casino.: This holiday home rental outside of South Boston has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.