Photo by kristy in VA

Holiday Rentals in South Boston

Start date: Check-in selected.
To Date
End date: Check-out
    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

In two weeks
In one month
In two months
In three months

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!

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

9.8 out of 10, Exceptional, (34)
"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

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

2.0 star property
9.8 out of 10, Exceptional, (9)
"We really enjoyed the lake house. Loved the location. Host was great! Hope to come back soon!! "
Kerr/Buggs Island Lake waterfront home w/dock, just off main channel!

Walking Distance to Casino

10.0 out of 10, Exceptional, (24)
"It is a very nice little home with a well thought out layout. Check in and out were super smooth and the bed was very comfortable. Will stay again when we come to town. "
The price is €363
includes taxes & fees
1 Oct - 2 Oct
Walking Distance to Casino

Mayo Lake Lower Unit Highend, Clean, Updated

10.0 out of 10, Exceptional, (94)
"Well maintained property, beautiful lake view. Quick access to town and dining. Brought our paddle boards and walked them down to the lake, which was really nice since the lake did not have many boaters. "
The price is €147
includes taxes & fees
1 Oct - 2 Oct
Mayo Lake Lower Unit Highend, Clean, Updated

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

9.8 out of 10, Exceptional, (158)
"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

Historic 2 br & 2 ba On the River

9.6 out of 10, Exceptional, (43)
"Pleasant experience."
Historic 2 br & 2 ba On the River

Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

10.0 out of 10, Exceptional, (96)
"We enjoyed our stay and loved the cabin."
Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

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

10.0 out of 10, Exceptional, (171)
"Cottage on the cove is one of the best homes we’ve stayed in. The house is extremely well stocked, the lake is gorgeous, with really great fishing, and there is enough around in the surrounding area to venture out for days trips if needed. We highly recommend staying here."
"Cottage On The Cove" Private Lakefront Paradise with Paddleboards & Kayaks

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

10.0 out of 10, Exceptional, (186)
"Second year staying here for a family gathering. Great space and location."
Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach

The Cedar Farm Close To VIR, Danville

10.0 out of 10, Exceptional, (34)
"Our stay was wonderful! The property was as described—clean, comfortable, and well-equipped with everything we needed. The host was responsive and made the check-in process seamless. The location was great, and we had a pleasant and relaxing experience. Would definitely stay again!"
The Cedar Farm Close To VIR, Danville

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!

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

9.8 out of 10, Exceptional, (31)
"Perfect location to the casino and restaurants. We loved our stay. "
The price is €228
includes taxes & fees
1 Oct - 2 Oct
Located in Historic Old West End. Minutes from the River District and Casino.

Historic 2 br & 1 ba On the River

9.6 out of 10, Exceptional, (45)
"I’ve stayed in this particular unit twice now (as well as 1 time in the unit next door) and all my stays with this host have been wonderful."
Historic 2 br & 1 ba On the River

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

9.6 out of 10, Exceptional, (91)
"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

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

Cozy home near golf & casino! in tranquil Danville

6.0 out of 10, (2)
"The state there was excellent the property and every essential you can think of was fully loaded the only issue was the code process. We got locked out and it tried to reach property manager and could not so we reached out to BRBO and they contacted him but with no avail we were unsuccessful however we did manage to get into the"
The price is €577
includes taxes & fees
1 Oct - 2 Oct
Cozy home near golf & casino! in tranquil Danville

Boutique Guest Stay in Downtown Clarksville

9.6 out of 10, Exceptional, (10)
"This was our second stay at this property and we thoroughly enjoyed it again!The property is clean, and the communication with the host was excellent. The people of Clarksville are so kind and welcoming. The location is great for lake activities, or exploring the area. We found some great local breweries and vinyards within reasonable distance and of course enjoyed Buggs Island Brewery for live music lakeside in the evenings. Highly recommend!!"
The price is €316
includes taxes & fees
6 Oct - 7 Oct
Boutique Guest Stay in Downtown Clarksville

WATERFRONT LOG HOME FOR FAMILY CHRISTMAS! HOT TUB/FIREPLACES/LARGE DECK/FIRE PIT

9.6 out of 10, Exceptional, (71)
"Awesome entertainment center, access to lake, hot tub,close to town averall good stay"
WATERFRONT LOG HOME FOR FAMILY CHRISTMAS! HOT TUB/FIREPLACES/LARGE DECK/FIRE PIT

Backwoods Guesthouse Near VIR and Hycolake

2.0 star property
9.8 out of 10, Exceptional, (6)
"Very secluded and quiet! Easy check in and out. Very nice inside, could use a TV, at least in the living room."
Backwoods Guesthouse Near VIR and Hycolake
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

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, apart-hotels, 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 favorite 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 depends 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 €147 per night. Entering your travel dates in the search wizard you might find 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.