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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!

Walking Distance to Casino

10.0 out of 10, Exceptional, (21)
"Fantastic two bedroom house, up to date, extremely clean, great televisions, well stocked. Highly recommend! "
The price is £224
includes taxes & fees
13 Aug - 14 Aug
Walking Distance to Casino

Cute Lakefront Cottage

9.8 out of 10, Exceptional, (52)
"Great place for our needs. Host is very accommodating. "
Cute Lakefront Cottage

H2O-FRONT Chef’s_Kitchen Gig-WiFi DogsOK EV-Charger Alexa

9.8 out of 10, Exceptional, (90)
"Beautiful location on the lake!!"
H2O-FRONT Chef’s_Kitchen Gig-WiFi DogsOK EV-Charger Alexa

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!

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

10.0 out of 10, Exceptional, (183)
"Great accommodations!"
Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach

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

10.0 out of 10, Exceptional, (171)
"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

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

9.6 out of 10, Exceptional, (155)
"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

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 £201
includes taxes & fees
13 Aug - 14 Aug
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

9.6 out of 10, Exceptional, (90)
"Very accommodating house, great spot on the lake"
Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly

Historic 2 br & 2 ba On the River

9.6 out of 10, Exceptional, (39)
"Loved the place! It was a great space - and great neighborhood! Would definitely stay there again!"
Historic 2 br & 2 ba On the River

Vacation home just 4 minutes drive to Caesars Virginia Casino

10.0 out of 10, Exceptional, (5)
"Perfect house to get a night out at the casino."
The price is £223
includes taxes & fees
13 Aug - 14 Aug
Vacation home just 4 minutes drive to Caesars Virginia Casino

Rustic Red Cabin on Kerr Lake

10.0 out of 10, Exceptional, (1)
"Enjoyed this place...rustic but has lots of great views, comfort and places to chill. Dog friendly, too but don't trust GPS. Go right at dumpster...not left and don't turn on Stuckornot Rd! Honestly, I hated to leave...and the OBX us my home! LolIf you enjoy a woodsy escape, this is your place."
Rustic Red Cabin on Kerr Lake

Historic 2 br & 1 ba On the River

9.8 out of 10, Exceptional, (44)
"This is a lovely property. We gladly recommend to travelers"
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, (92)
"We enjoyed our stay and loved the cabin."
Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

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!

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 £175
includes taxes & fees
3 Sept - 4 Sept
Coleman 202 RD travel trailer. Located on the owner's lakefront property!

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

9.8 out of 10, Exceptional, (30)
"Beautiful home, comfortable beds, spacious kitchen/living area. Great location! We plan to book again!"
Bring YOUR BOAT- Private Dock, Deep Water, Gameroom and Firepit

Private Lakefront Log Cabin

10.0 out of 10, Exceptional, (140)
"Graet spot for fishing and peace of mind. "
Private Lakefront Log Cabin

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

9.4 out of 10, Exceptional, (13)
"My family had a wonderful stay at this property while in town to celebrate my daughter’s graduation from Averett University. This is a nicely renovated property in a quiet older neighborhood. It was spacious enough to host our large family and had a lot of amenities to keep everyone entertained. We enjoyed the in-ground pool, large charcoal grill and pool house out back as well as games in the basement and tv’s in every room. It was near the university, shopping, restaurants and the new Caesar’s...
Dan River Chateau-In ground swimming pool great for hosting or relaxing
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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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?

Walking Distance to Casino: This holiday home rental outside of South Boston offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 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?

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.