South Boston Holiday Rentals

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Holiday Rentals in South Boston

Holiday Home in Charlestown

10.0 out of 10, Exceptional, (3)
"This a great place for families to gather. It's very spacious and clean and comfortable. And though it's in a quiet and peaceful area with a small lake at the base of the property, places to eat and get groceries are just a short drive away. There's a wonderful seating area around a firepit, too!"
United States
Kelly P.
The price is AU$710
includes taxes & fees
21 Nov - 22 Nov
Emerald Lake Retreat Charlestown

Cabin in Orleans

10.0 out of 10, Exceptional, (183)
"quiet. clean. beautiful property for this cabin setting"
United States
Denise
The price is AU$297
includes taxes & fees
20 Nov - 21 Nov
Cozy Country Cabin quiet country retreat

Apartment in Memphis

10.0 out of 10, Exceptional, (12)
"Was the perfect little overnight stay! "
United States
Billie Jo M.
The price is AU$246
includes taxes & fees
26 Nov - 27 Nov
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

Holiday Home in Scottsburg

9.0 out of 10, Wonderful, (2)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is AU$292
includes taxes & fees
15 Dec - 16 Dec
Cozy Tiny House in Scottsburg

Cabin in Henryville

10.0 out of 10, Exceptional, (153)
"This is beautiful property and thoughtful amenities. The host is super responsive. We cannot wait to plan our next stay. "
United States
Katie A.
The price is AU$658
includes taxes & fees
20 Nov - 21 Nov
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Holiday Home in Henryville

10.0 out of 10, Exceptional, (26)
"Can’t say enough good things about this place!"
United States
Christal C.
The price is AU$390
includes taxes & fees
30 Nov - 1 Dec
Country home with beautiful views and access to hiking, biking, and horse trails

Holiday Home in Vallonia

2.0 star property
10.0 out of 10, Exceptional, (13)
"Excellent place to stay. Everything was absolutely amazing. "
United States
Jimmy
The price is AU$442
includes taxes & fees
1 Dec - 2 Dec
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

Cottage in New Pekin

The price is AU$732
includes taxes & fees
22 Nov - 23 Nov
Charming 2-bedroom cottage with WiFi, AC in wonderful New Pekin

Cottage in Palmyra

6.0 out of 10, (1)
"Beautiful land and venue with great location! Absolutely loved those aspects and would’ve given it more stars if there were no concerns. The only issues we had were regarding cleanliness (a very strong mold smell resulting from a kitchen sink leak in the cabinet below) and pest infestations in the kitchen. Both were communicated to the property manager who advised they relayed them to the owners. We made it work as we weren’t at the house much at all, but it would have been very nice to receive...
United Kingdom
Stephanie C.
The price is AU$415
includes taxes & fees
20 Nov - 21 Nov
Moonlit Cottage Near Louisville

Holiday Home in Hardinsburg

10.0 out of 10, Exceptional, (37)
"We love staying here for our annual Kayak trip!"
United States
Joni D.
The price is AU$933
includes taxes & fees
20 Nov - 21 Nov
Tell your family to meet you here!<br>No Drinking Parties

Holiday Home in Salem

"This is a lovingly restored historical property with many beautiful original features, like the staircase & railings. The little town is so nice, and the people are friendly. We came down from Georgia to help a family member move into the home they just bought and needed a comfortable place to stay after moving stuff all day. We all decided we need to come for a longer time so we can check out all the interesting historical site nearby. We ate out every day & only used the coffee maker but the...
United States
Elizabeth
The price is AU$506
includes taxes & fees
24 Nov - 25 Nov
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
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$246 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 a holiday rental in South Boston?

Yes, there are holiday rentals close to the most popular sights in South Boston, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that South Boston has to offer?

Cozy Tiny House in Scottsburg: This holiday home rental outside of South Boston has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in South Boston?

Explore the area and family-friendly sights such as Kentuckiana Trading, or get out into nature at a spot like Deam Lake State Recreation Area. Champions Pointe Golf Club and Huber’s Orchard, Winery & Vineyards are a couple of places you'll find in the wider area.

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 extras such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for small groups.