Photo by kristy in VA

South Boston Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

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, (24)
"Perfect location to the casino and restaurants. We loved our stay. "
The price is AU$398
includes taxes & fees
6 Aug - 7 Aug
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, (154)
"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

Walking Distance to Casino

10.0 out of 10, Exceptional, (20)
"We loved the updates to the property. We appreciate the host’s hospitality! "
The price is AU$436
includes taxes & fees
5 Aug - 6 Aug
Walking Distance to Casino

Cute Lakefront Cottage

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

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

10.0 out of 10, Exceptional, (181)
"Great accommodations!"
Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach

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

9.6 out of 10, Exceptional, (89)
"Very accommodating house, great spot on the lake"
Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"This perfectly sized house overlooking a lake, was also convenient to downtown Clarksville. We would definitely stay again!"
Kerr Lake waterfront home w/dock, just off main channel, close to town!

Hidden Haven - Hot Tub, Outdoor Shower & Firepit

9.6 out of 10, Exceptional, (18)
"We thoroughly enjoyed our visit and would recommend highly!"
Hidden Haven - Hot Tub, Outdoor Shower & Firepit

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!

Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

10.0 out of 10, Exceptional, (92)
"We enjoyed our stay and loved the cabin."
Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

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

10.0 out of 10, Exceptional, (32)
"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

"Cottage On The Cove" Private Lakefront Paradise with Paddleboards & Kayaks

10.0 out of 10, Exceptional, (170)
"Absolutely fabulous views of the lake and well furnished both inside and out. Comfortable furniture and excellent mattresses and pillows. Hosts were easy to communicate with and very responsive. We will definitely stay again!"
"Cottage On The Cove" Private Lakefront Paradise with Paddleboards & Kayaks

Lakefront Leasburg Home w/ Dock & Views!

10.0 out of 10, Exceptional, (13)
"Luxury in the Ruff.lol Me the family and the Lil puppy Just comfy enough the lake life is good. Highly recommend.."
Lakefront Leasburg Home w/ Dock & Views!

Vacation home just 4 minutes drive to Caesars Virginia Casino

10.0 out of 10, Exceptional, (4)
"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. "
The price is AU$441
includes taxes & fees
6 Aug - 7 Aug
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, (6)
"The property was as advertised. Therecwere two pro"
Single-Story Cabin on Hyco Lake: Swim & Unwind!

Lakefront, Great Views, Hot Tub, Boat Options

9.8 out of 10, Exceptional, (94)
"This is a very nice spacious property. The host Jeremy were pleasant and prompt."
Lakefront, Great Views, Hot Tub, Boat Options

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

9.8 out of 10, Exceptional, (10)
"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, (3)
"As a person who travels alot for work and normally stays in a chain hotel room, I was extremely impressed with this property - it is clean, well appointed, quite comfortable and in a convenient location. I highly recommend this property!!"
Renovated 1BR - 3 Block Walk to Casino - Clean, Quiet, Safe & Guest-Favorite

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.
Save an average of 15% on thousands of hotels when you're signed in

Top South Boston Hotel Reviews

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?

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 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.