Photo by kristy in VA

South Boston Holiday Rentals

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Holiday Rentals in South Boston

Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

10.0 out of 10, Exceptional, (76)
"The cabin is beautiful. We walked all through the neighborhood and into town. Had a great time sitting on the screened in porch wt a fire, talking and catching up wt family. Hope to do this again soon. Host was easy to contact for any questions I had. Thank you so much. God Bless. "
Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

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

10.0 out of 10, Exceptional, (168)
"This is a very nice place. Plenty of room for 6 adults. Great location, short drive to anything you could need, shopping and restaurants. If you are in the area for fishing you are just a short drive to several different boat landing."
Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach

Cozy Cottage in Schoolfield - Sleeps 6 - 10 min walk to Caesars Virginia

9.6 out of 10, Exceptional, (17)
"Rented this property because my niece was getting married at Hyco Lake. The property is amazing and conveniently located very close ti the casino."
The price is AU$271
includes taxes & fees
4 Dec - 5 Dec
Cozy Cottage in Schoolfield - Sleeps 6 - 10 min walk to Caesars Virginia

Solar powered lake cottage with dock on private 300 acre preserve

9.8 out of 10, Exceptional, (147)
"What a cute little cabin in the woods! Exactly as described. The amazing weather made sitting on the dock was breath taking. If you are looking for seclusion this is it. We are very happy customers. "
Solar powered lake cottage with dock on private 300 acre preserve

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

9.6 out of 10, Exceptional, (10)
"Such a great place ro stay. We were thrilled with the house the moment we opened the front door. Beautifully decorated and super clean in a well established neighborhood. We would definitely stay again. "
The price is AU$438
includes taxes & fees
24 Nov - 25 Nov
Located in Historic Old West End. Minutes from the River District and Casino.

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

9.4 out of 10, Exceptional, (82)
"What a beautiful spot to relax and recharge. The surrounding area is just spectacular. It is a perfect place to unplug, take a breath and connect with nature. "
Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly

Lake Front Home on Buggs Island / Kerr Lake<br>Close to Bluestone Boat Ramp!

10.0 out of 10, Exceptional, (14)
"We really enjoyed our first time at this house in Clarksville. We always love our trips to Bugg's Island and this house did not disappoint!!!! Pros: Very clean, easy access to town, great communication with the owners prior to arrival. We didn't have any issues or concerns during our stay. Loved the owners laminated reminders for check-in and check-out ~ made taking care of their house a breeze. The house provided all the kitchen appliances you would need for eating at home and grilling out....
Lake Front Home on Buggs Island / Kerr Lake<br>Close to Bluestone Boat Ramp!

Peaceful Chatham Home w/ Grill & Deck

10.0 out of 10, Exceptional, (6)
"We had such a great experience. Jennifer was so helpful. Yall had thought of everything. Even down to us locking ourselves out. lol. The location and the house was perfect. We even saw some deer in the backyard. We will have this place saved if we get to make it back to Chatham in the future. "
Peaceful Chatham Home w/ Grill & Deck

6 Bedrooms, Lakefront, Hot-Tub & Private Dock

9.0 out of 10, Wonderful, (13)
"Great house and great location. We enjoyed our stay."
6 Bedrooms, Lakefront, Hot-Tub & Private Dock

12 Mi to Staunton River: Nathalie Cabin w/ Deck

10.0 out of 10, Exceptional, (5)
"We loved the Cabin, sitting back in the back part of what appeared to be 25-30 Acres, in a county pasture setting. As you entered the property there was a beautiful fence line w/ roll hay bales across the front, with some fall decorations in front. The Cabin was awesome inside, really county home setting inside with different types of farm house amenities. We contacted the PoC “ Skeeter” who had the Cabin open when we arrived. The information paper for guest provided was detailed . This is a...
12 Mi to Staunton River: Nathalie Cabin w/ Deck

Lakefront, Great Views, Hot Tub, Boat Options

9.8 out of 10, Exceptional, (87)
"This was our second time renting this house, we love everything about it. It's so peaceful and beautiful. The kids love going fishing and kayaking. The house has plenty of space for our large family and lots to do inside as well."
Lakefront, Great Views, Hot Tub, Boat Options

NEW RATES: Miles to VIR, Caesar's VA Casino, Martinsv'l , S.Boston, Priv. Pool

9.8 out of 10, Exceptional, (30)
"Always a joy to stay here! We look forward to coming back again some day soon!"
NEW RATES: Miles to VIR, Caesar's VA Casino, Martinsv'l , S.Boston, Priv. Pool

Historic 2 br & 1 ba On the River

9.8 out of 10, Exceptional, (29)
"Loved being in the downtown area. Great place to stay. Definitely recommend."
Historic 2 br & 1 ba On the River

Dan River Chateau-In ground swimming pool great for hosting or relaxing

9.8 out of 10, Exceptional, (9)
"The house is great. We enjoyed playing air hockey in the very nice basement. The backyard is amazing! Very big yard with pool and privacy fence. The lights in the backyard at night are beautiful and a great spot to relax and wind down. We loved it and already booked it again! The host is just great!"
Dan River Chateau-In ground swimming pool great for hosting or relaxing

Majestic Lakefront Log Cabin located in the NC High Plains

10.0 out of 10, Exceptional, (76)
"Everything was just as described. We like low key, hang at a house, fish, and play table games type places and this was perfect. Felt secluded, but town is close if you need anything and the little section of the lake was so peaceful! Fans were nice outside on the covered porch and the dock/pontoon was good for 4 people to fish off of. Only 1 1/2 hrs from Raleigh, which was a plus since family was coming up from State. GO PACK!"
Majestic Lakefront Log Cabin located in the NC High Plains

Mansion on Main | Danville Vacation Rental

8.6 out of 10, Excellent, (4)
"It is an old house, as stated in the ad. Some rooms had bad smell, especially the BR in the basement. Lots of room for everything. We had minor plumbing and electrical issues. Some of the bedrooms were inter connected, had privacy issues. Disappointed with the pool, as it was not clean despite the efforts from two people who came to clean it. Overall it was good!"
Mansion on Main | Danville Vacation Rental

Modern Victorian Home across Averett University

10.0 out of 10, Exceptional, (18)
"Great house, just as advertised! Would definitely stay again"
Modern Victorian Home across Averett University

Hideaway Haven - Hot Tub, Firepit & Private Dock

9.4 out of 10, Exceptional, (16)
"We always have a relaxing and wonderful time here. Thank you for sharing your home. "
Hideaway Haven - Hot Tub, Firepit & Private Dock

Bring YOUR BOAT- Private Dock, Deep Water, Gameroom and Firepit

10.0 out of 10, Exceptional, (24)
"There were 8 family members that stayed here as we traveled in for my daughter's wedding. The layout of the house was perfect and very roomy that allowed us to spread out and made getting ready on the wedding day a breeze. Upon arrival, the house was clean for the most part. The front porch could use a good cleaning. The stairs to the basement are very steep and the overhand is low. The first day, someone hit their head going down the stairs. I would recommend a sign to warn people. Overall the...
Bring YOUR BOAT- Private Dock, Deep Water, Gameroom and Firepit

Historic 1br 1ba On the River!

9.0 out of 10, Wonderful, (4)
"We enjoyed our stay, walkable to restaurants and walking/bike trail. The apartment was super cute, had everything we needed."
Historic 1br 1ba On the River!
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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Other types of properties in South Boston you may be interested in

The Berry Hill Resort & Conference Center

4.0 star property
9.2 out of 10, Wonderful, (595)
"I love the romantic environment. "
The price is AU$287
includes taxes & fees
24 Nov - 25 Nov
The Berry Hill Resort & Conference Center

Americas Best Value Inn & Suites South Boston

2.0 star property
5.6 out of 10, (223)
"No internet for the night"
The price is AU$94
includes taxes & fees
24 Nov - 25 Nov
Americas Best Value Inn & Suites South Boston

Clarion Pointe South Boston - Danville East

3.5 star property
7.4 out of 10, Good, (199)
"Great "
The price is AU$164
includes taxes & fees
8 Dec - 9 Dec
Clarion Pointe South Boston - Danville East
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.
Beautiful view of the beach with palm trees

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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 Halifax County Fairgrounds, 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?

Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly: 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 a garden and 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?

Hudson Heritage Farms and Tobacco Heritage Trail - Cotton Mill Park Trailhead, South Boston are a couple of lovely local spots to get outside and enjoy nature. South Boston Speedway and South Boston Town Hall 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.