South Boston Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for South Boston holiday rentals

Cozy Country Cabin quiet country retreat

Cozy Country Cabin quiet country retreat
Orleans
10.0 out of 10, Exceptional, (189)
"We really enjoyed our stay. The cabin is very nice and so is the pond."
United States
Scott H.
The price is NZ$328
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy Country Cabin quiet country retreat

Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (4)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is NZ$302
includes taxes & fees
29 Dec - 30 Dec
Cozy Tiny House in Scottsburg

Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
Memphis
10.0 out of 10, Exceptional, (14)
"Property was very clean, smelt great, and spacious. Located in a nice neighborhood. Hosts were extremely accommodating and friendly. Would definitely stay here again if I'm back in the area for an overnight trip. "
United States
Mandy M.
The price is NZ$271
includes taxes & fees
29 Dec - 30 Dec
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb
4.0 star property
Sellersburg
9.4 out of 10, Exceptional, (10)
"Very nice house in a nice neighborhood, spacious home environmental, felt more that at home there,"
United States
Tammy
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

Moonlit Cottage Near Louisville

Moonlit Cottage Near Louisville
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 NZ$429
includes taxes & fees
29 Dec - 30 Dec
Moonlit Cottage Near Louisville

Emerald Lake Retreat Charlestown

Emerald Lake Retreat Charlestown
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 NZ$784
includes taxes & fees
30 Dec - 31 Dec
Emerald Lake Retreat Charlestown

Country home with beautiful views and access to hiking, biking, and horse trails

Country home with beautiful views and access to hiking, biking, and horse trails
Henryville
10.0 out of 10, Exceptional, (30)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
The price is NZ$466
includes taxes & fees
19 Jan - 20 Jan 2026
Country home with beautiful views and access to hiking, biking, and horse trails

Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
2.0 star property
Vallonia
10.0 out of 10, Exceptional, (14)
"Excellent place to stay. Everything was absolutely amazing. "
United States
Jimmy
The price is NZ$510
includes taxes & fees
30 Dec - 31 Dec
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
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 NZ$819
includes taxes & fees
4 Jan - 5 Jan 2026
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Charming 2-bedroom cottage with WiFi, AC in wonderful New Pekin

Charming 2-bedroom cottage with WiFi, AC in wonderful New Pekin
New Pekin
The price is NZ$807
includes taxes & fees
31 Dec - 1 Jan 2026
Charming 2-bedroom cottage with WiFi, AC in wonderful New Pekin

Tell your family to meet you here!<br>No Drinking Parties

Tell your family to meet you here!<br>No Drinking Parties
Hardinsburg
10.0 out of 10, Exceptional, (37)
"We love staying here for our annual Kayak trip!"
United States
Joni D.
The price is NZ$1,029
includes taxes & fees
7 Jan - 8 Jan 2026
Tell your family to meet you here!<br>No Drinking Parties

The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
Salem
10.0 out of 10, Exceptional, (2)
"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 NZ$581
includes taxes & fees
5 Jan - 6 Jan 2026
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.
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

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 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 NZ$271 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 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.