Photo by kristy in VA

South Boston Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in South Boston

A roomy, comfortable home close to everything.
10.0 out of 10, Exceptional, (4)
"I met a friend in South Boston for an art event. Having never visited the area we decided to stay two nights in order to have more time to explore. Originally we had three people in our group so we had an extra bedroom that we didn’t use. We had some confusion about the code to access the key and the host was there to help us within five minutes. The people that we met in the town were very nice. I would have to say that the town is smaller than I expected, but we also visited Danville and...
A roomy, comfortable home close to everything.
WATERFRONT LOG HOME w/ HOT TUB, 2 FIREPLACES, FIRE PIT, 77" TV SURROUND SOUND!
9.6 out of 10, Exceptional, (61)
"What a wonderful place to stay. We enjoyed the house. It was perfect for hosting our daughter’s little birthday party. Very convenient to the lake, gas station, dollar general and Clarksville shopping. Super nice property owners. Very accommodating!"
WATERFRONT LOG HOME w/ HOT TUB, 2 FIREPLACES, FIRE PIT, 77" TV SURROUND SOUND!
Modern Victorian Home across Averett University
10.0 out of 10, Exceptional, (12)
"Recital weekend at Averrett University, house was only a 5 minute walk from the venue. House was as described, we had plenty of room for getting ready and the house was beautifully lit at night when we returned. Would recommend if needing something close to the University, however parking is very limited to 2 vehicles only!"
The price is NZ$556
includes taxes & fees
2 Jun - 3 Jun
Modern Victorian Home across Averett University
Save an average of 15% on thousands of hotels when you're signed in
Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly
9.6 out of 10, Exceptional, (77)
"This is our third or fourth time staying here. Convenient location on bluestone creek. Close to Clarksville and within 15-20 min and shorter of all popular boat ramps. Plenty of boat parking for 4-5 boats. This is a must for a large group, no unhooking. This house has all the amenities one could ask for. All the kitchen utensils, two refrigerators, a grill, and much more! Thanks again Mathew for hosting us. You will see us again."
Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly
Bring YOUR BOAT- Private Dock, Deep Water, Gameroom and Firepit
10.0 out of 10, Exceptional, (18)
"Wonderful house and location"
Bring YOUR BOAT- Private Dock, Deep Water, Gameroom and Firepit
Lake Front Home on Buggs Island / Kerr Lake<br>Close to Bluestone Boat Ramp!
10.0 out of 10, Exceptional, (10)
"Beautiful house in a wonderful location. The hosts were very accommodating and responsive to any questions. If you’re looking for a lake house close to town with a beautiful view, this is the place to stay!"
Lake Front Home on Buggs Island / Kerr Lake<br>Close to Bluestone Boat Ramp!
Kerr Contentment Kerr Lake/Buggs Island waterfront, an amazing view
10.0 out of 10, Exceptional, (6)
"We had a wonderful Mother’s Day weekend on the lake! The house was exactly as listed. Plenty of space for all. Tons of amenities to keep us busy, if we wanted. And a lovely deck and lawn to just hang out and enjoy the view. Easy access to launch our boat from a nearby park. And ample space to tie up on the private dock. We took advantage of the excellent fishing Kerr Lake has to offer. We thoroughly enjoyed our stay. We highly recommend if you are looking for a quiet time on the lake but still...
Kerr Contentment Kerr Lake/Buggs Island waterfront, an amazing view
Historic 2 br & 1 ba On the River
10.0 out of 10, Exceptional, (19)
"Another pleasant stay. Always quite. Found some very food spots on the Main Street. Green Leaf and Cotton also Taco BBQ .. great smoked wings!!"
The price is NZ$429
includes taxes & fees
2 Jun - 3 Jun
Historic 2 br & 1 ba On the River
Solar powered lake cottage with dock on private 300 acre preserve
9.6 out of 10, Exceptional, (134)
"If you read and loved the description of this place, you will, indeed, love this place. It's exactly what's advertised and it has been the perfect getaway for my husband and me twice now. Its a gorgeous location with ample fishing, reading, lazing opportunities. The cabin is adorable, the bed is comfy, the fire pit is awesome! There's so much to love about this place. We will be back every time we get the opportunity."
Solar powered lake cottage with dock on private 300 acre preserve
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
Hyco Lake Hideout - amazing location!
9.0 out of 10, Wonderful, (2)
"The place was very nice. Was clean and well taken care of. Would definitely recommend and will definitely return."
Hyco Lake Hideout - amazing location!
Cozy cabin w/ hot tub! Lake access w/ walk to pier
10.0 out of 10, Exceptional, (3)
"We had an amazing time. We really enjoyed the cozy red couch and all the little bear touches all over the home."
Cozy cabin w/ hot tub! Lake access w/ walk to pier
Church of the Perpetual Boogie: near VIR & Casino
10.0 out of 10, Exceptional, (1)
"even better than the pics.. Thanks again!!"
The price is NZ$924
includes taxes & fees
4 Jun - 5 Jun
Church of the Perpetual Boogie: near VIR & Casino
Rustic Lakehouse Oasis - Hot Tub, Game Room, Fire Pit, and Fishing Rods
10.0 out of 10, Exceptional, (8)
"My family & friends stayed at this beautiful lake house for my son's wedding. It was absolutely perfect! Although we weren't able to enjoy all of the amenities offered, I would definitely book it again for a relaxing weekend with friends/family."
The price is NZ$772
includes taxes & fees
26 Jun - 27 Jun
Rustic Lakehouse Oasis - Hot Tub, Game Room, Fire Pit, and Fishing Rods
Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA
10.0 out of 10, Exceptional, (61)
"Jim and Mona are the best host! They make sure you have what you need and always go above and beyond. The dog park is a great addition and so convenient. We love being able to walk to town and back. The dock has plenty of room to hang out and just relax in the water. It is covered so if you need to get out of the sun you are able too."
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, (157)
"Great Cabin, nice location and super nice hosts! Hope to stay again sometime. Thanks!!"
Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach
Hyco lakefront rental that's very close to VIR! Quiet cove to come and relax.
10.0 out of 10, Exceptional, (10)
"Great place for a group. Close to VIR. Beds were comfortable. Kitchen was well stocked. The pellet grill was perfect for cooking a few steaks."
Hyco lakefront rental that's very close to VIR! Quiet cove to come and relax.
Waterfront: Caiman Cove
9.4 out of 10, Exceptional, (8)
"We had a great time. The dock was great to fish off of or just relax and enjoy the scenery. The air conditioning did a fantastic job and the place was very clean. There were plenty of towels available. The kitchen was very well equipped. Overall we enjoyed this house. If you are looking for a secluded, relaxing getaway, this is the place for you."
Waterfront: Caiman Cove
Cozy Cottage in Schoolfield - Sleeps 6 - 10 min walk to Caesars Virginia
8.8 out of 10, Excellent, (6)
"Lovely little remodeled cottage! Attention to detail showed! Great stay! Highly recommend!!"
The price is NZ$280
includes taxes & fees
3 Jun - 4 Jun
Cozy Cottage in Schoolfield - Sleeps 6 - 10 min walk to Caesars Virginia
Family friendly home on Hyco Lake, large dock, fire pit, one level.
10.0 out of 10, Exceptional, (1)
"Stayed at this lovely lake property just 10 minutes from VIR. Lovely place, well appointed, and super convenient for racing at VIR! Will use again!"
Family friendly home on Hyco Lake, large dock, fire pit, one level.
Don't see what you're looking for?
See all available properties in South Boston
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.

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, (507)
"As always, clean, quiet and convenient. "
The price is NZ$300
includes taxes & fees
2 Jun - 3 Jun
The Berry Hill Resort & Conference Center
Americas Best Value Inn & Suites South Boston
2.0 star property
5.6 out of 10, (181)
"Overall environment"
The price is NZ$100
includes taxes & fees
2 Jun - 3 Jun
Americas Best Value Inn & Suites South Boston
Quality Inn South Boston - Danville East
2.5 star property
7.4 out of 10, Good, (302)
"Overall great "
The price is NZ$156
includes taxes & fees
9 Jun - 10 Jun
Quality Inn 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our South Boston holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up South Boston. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in South Boston. Seeing all the best attractions is bound to make you fall in love with South Boston. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in South Boston short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in South Boston?

Yes, there are holiday rentals close to the most popular sights in South Boston, 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 w/ HOT TUB, 2 FIREPLACES, FIRE PIT, 77" TV SURROUND 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?

Enjoy the area's cultural attractions such as L. E. Coleman African-American Museum, or get outdoors into nature at a spot like Hudson Heritage Farms. In the wider area, you’ll find South Boston Speedway and Staunton River State Park.

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.

Recent reviews of South Boston properties
Expedia verified reviews