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South Boston Holiday Rentals

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Holiday Rentals in South Boston

Our top choices for South Boston holiday rentals

2 Mi to South Boston Speedway: Cozy Tiny Home!

3.0 star property
2 Mi to South Boston Speedway: Cozy Tiny Home!

Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

10.0 out of 10, Exceptional, (94)
"We enjoyed our stay and loved the cabin."
Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

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

9.6 out of 10, Exceptional, (155)
"Great location. Atmosphere. And overall vibe. Cant wait to Hopefully Go Again!"
Solar powered cottage at lake, with dock, on private 300 acre timber preserve

Kerr/Buggs Island Lake waterfront home w/dock, just off main channel!

2.0 star property
9.8 out of 10, Exceptional, (6)
"This perfectly sized house overlooking a lake, was also convenient to downtown Clarksville. We would definitely stay again!"
Kerr/Buggs Island Lake waterfront home w/dock, just off main channel!

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

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

9.8 out of 10, Exceptional, (93)
"Beautiful location on the lake!!"
H2O-FRONT Chef’s_Kitchen Gig-WiFi DogsOK EV-Charger Alexa

Walking Distance to Casino

10.0 out of 10, Exceptional, (23)
"Fantastic two bedroom house, up to date, extremely clean, great televisions, well stocked. Highly recommend! "
The price is AU$781
includes taxes & fees
4 Sept - 5 Sept
Walking Distance to Casino

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

Historic 2 br & 2 ba On the River

9.6 out of 10, Exceptional, (41)
"Pleasant experience."
Historic 2 br & 2 ba On the River

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

9.8 out of 10, Exceptional, (27)
"Perfect location to the casino and restaurants. We loved our stay. "
The price is AU$404
includes taxes & fees
7 Sept - 8 Sept
Located in Historic Old West End. Minutes from the River District and Casino.

Home featuring 3 Rooms 1 Bath Sleeps 6 Guest

10.0 out of 10, Exceptional, (2)
"The property was nice and clean. It’s future, three bedrooms, one bathroom, living room, space, laundry area, and kitchen. I rented this home for three nights and it was comfortable. I would stay here again."
The price is AU$328
includes taxes & fees
11 Sept - 12 Sept
Home featuring 3 Rooms 1 Bath Sleeps 6 Guest

Cozy retreat with lots of room for outdoor activities.

10.0 out of 10, Exceptional, (11)
"The place was very nice and clean. "
Cozy retreat with lots of room for outdoor activities.

Cute Lakefront Cottage

9.8 out of 10, Exceptional, (54)
"Great place for our needs. Host is very accommodating. "
Cute Lakefront Cottage

Historic 2 br & 1 ba On the River

9.6 out of 10, Exceptional, (45)
"This is a lovely property. We gladly recommend to travelers"
Historic 2 br & 1 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 AU$455
includes taxes & fees
4 Sept - 5 Sept
Vacation home just 4 minutes drive to Caesars Virginia Casino

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

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

9.6 out of 10, Exceptional, (90)
"Went with family a friends. Lovely house, two docks were nice just a little bit of a walk to get to them but there was a nice cleared path way to get to them. Would definitely stay again. "
Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly

Lakefront with Million Dollar Views on HYCO Lake

10.0 out of 10, Exceptional, (5)
"We have stayed at many vrbo rentals and this was the most furnished and best experience we have had. Very clean maintained and up to date. Host was on the ball. We had a storm roll through and knocked out the Internet, within 30 minutes of calling him He had his back up and running……Spent a lot of time fishing caught bass, crappie, bream, shell cracker and channel catfish. Thank you very much. Boat house wonderful. "
Lakefront with Million Dollar Views on HYCO Lake

"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

Church of the Perpetual Boogie: near VIR & Casino

10.0 out of 10, Exceptional, (10)
"We really enjoyed our stay!"
The price is AU$990
includes taxes & fees
4 Sept - 5 Sept
Church of the Perpetual Boogie: near VIR & Casino
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

Find out more about South Boston

Find out more about South Boston

Everything you need to know about South Boston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Boston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Boston holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

South Boston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Boston. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Boston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Boston holiday rentals we have selected for you start as low as AU$328 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on South Boston rentals

At Expedia, we put the best South Boston holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top South Boston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Boston holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Boston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Kerr/Buggs Island Lake waterfront home w/dock, just off main channel!: This holiday home rental outside of South Boston is located on a lake, and has a fireplace, a balcony and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. 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.