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South Boston Holiday Rentals

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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!
Studio 2 Mi to South Boston Speedway
3.0 star property
Studio 2 Mi to South Boston Speedway
H2O-FRONT Chef’s_Kitchen Gig-WiFi DogsOK EV-Charger Alexa
9.8 out of 10, Exceptional, (93)
"Our family enjoyed our stay very much! Having multiple bathrooms was a big plus. We had a wonderful time on the lake. The kitchen is amazing! The amount of things available in the house for our use was beyond great! Wow describes how we felt about everything! We hope to repeat our visit ar some point. Rick was always available when I had questions and that was very much appreciated."
United States
Teresa Z.
H2O-FRONT Chef’s_Kitchen Gig-WiFi DogsOK EV-Charger Alexa
Mayo Lake Lower Unit Highend, Clean, Updated
9.8 out of 10, Exceptional, (98)
"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. "
United States
Ryan C.
Mayo Lake Lower Unit Highend, Clean, Updated
Bring YOUR BOAT- Private Dock, Deep Water, Gameroom and Firepit
9.8 out of 10, Exceptional, (34)
"Owner interaction was excellent in planning the trip. Thank you for the nice welcome basket of goodies. The toys were great for the children. Overall the stay was very nice."
United States
Christina C.
Bring YOUR BOAT- Private Dock, Deep Water, Gameroom and Firepit
Walking Distance to Casino
10.0 out of 10, Exceptional, (25)
"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. "
United States
Chris H.
The price is AU$728
includes taxes & fees
16 Nov - 17 Nov
Walking Distance to Casino
Solar powered cottage at lake, with dock, on private 300 acre timber preserve
9.6 out of 10, Exceptional, (159)
"We enjoyed spending time down at the lake as did our dogs! "
United States
Holly G.
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.
9.8 out of 10, Exceptional, (31)
"Perfect location to the casino and restaurants. We loved our stay. "
United States
Gail
The price is AU$407
includes taxes & fees
20 Oct - 21 Oct
Located in Historic Old West End. Minutes from the River District and Casino.
Kerr/Buggs Island Lake waterfront home w/dock, just off main channel!
2.0 star property
9.8 out of 10, Exceptional, (11)
"We really enjoyed the lake house. Loved the location. Host was great! Hope to come back soon!! "
United States
Tammy A.
Kerr/Buggs Island Lake waterfront home w/dock, just off main channel!
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. "
United States
Samantha B.
Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly
LAKE VIEW! FISHERMANS DREAM! CLOSE TO BLUESTONE BOAT LANDING!
9.8 out of 10, Exceptional, (10)
"Perfect cottage for us to stay in across from the family home. "
United States
Joan and Jeff J.
LAKE VIEW! FISHERMANS DREAM! CLOSE TO BLUESTONE BOAT LANDING!
"Cottage On The Cove" Private Lakefront Paradise with Paddleboards & Kayaks
10.0 out of 10, Exceptional, (172)
"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."
United States
Kelly C.
"Cottage On The Cove" Private Lakefront Paradise with Paddleboards & Kayaks
Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA
10.0 out of 10, Exceptional, (97)
"We enjoyed our stay and loved the cabin."
United States
joseph d.
Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA
Cozy retreat with lots of room for outdoor activities.
10.0 out of 10, Exceptional, (11)
"This is a great property for a quiet time away from things. It's like camping with a large indoor space where you can eat, sleep, shower, and do laundry on site. The host responded quickly to any of our questions. We had to cut our stay short due to a health issue (unrelated to the property) and the host generously gave us a partial refund. Would recommend if you are looking for a place to rest and enjoy the outdoors."
United States
Ross N.
Cozy retreat with lots of room for outdoor activities.
Welcoming 3bd/2ba near Averett
10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay. This is a nice neighborhood, calm quiet. There is not much traffic on these streets, good for walking and if you are athletic or like a challenge, good for running hills! To me the rooms were more spacious than what they appear in the pictures. I love houses of this age and style, it has so much character.The host was easy to reach, if needed (although I did not need anything).There were spices, salt and pepper along with Saran Wrap, wax paper, etc, all the kitchen...
United States
Lil N.
Welcoming 3bd/2ba near Averett
Backwoods Milton House 3BR&2bath 3 Miles from VIR
2.0 star property
9.8 out of 10, Exceptional, (14)
"Very clean, conveniently located property. "
United States
Julie B.
Backwoods Milton House 3BR&2bath 3 Miles from VIR
Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach
10.0 out of 10, Exceptional, (187)
"Second year staying here for a family gathering. Great space and location."
United States
Gina G.
Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach
Log Cabin Retreat/Pet Friendly: Lake, Golf & Wine
2.0 star property
10.0 out of 10, Exceptional, (5)
"Great getaway place for couples or small families. "
United States
Tom H.
The price is AU$275
includes taxes & fees
20 Oct - 21 Oct
Log Cabin Retreat/Pet Friendly: Lake, Golf & Wine
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"
United States
Linda H.
The price is AU$2,104
includes taxes & fees
20 Oct - 21 Oct
Cozy home near golf & casino! in tranquil Danville
Vacation home just 4 minutes drive to Caesars Virginia Casino
10.0 out of 10, Exceptional, (6)
"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. "
United States
DEBRA K.
The price is AU$513
includes taxes & fees
20 Oct - 21 Oct
Vacation home just 4 minutes drive to Caesars Virginia 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

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$275 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.