South Boston Holiday Rentals

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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, (197 reviews)
"Fireplace was cozy Nice shower Comfortable furniture "
United States
James
The price is NZ$324
includes taxes & fees
18 May - 19 May
Cozy Country Cabin quiet country retreat

Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (7 reviews)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is NZ$299
includes taxes & fees
18 May - 19 May
Cozy Tiny House in Scottsburg

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
Vallonia
10.0 out of 10, Exceptional, (14 reviews)
"This place was great. We will be staying here if ever back in the area. "
United States
Michael B.
The price is NZ$501
includes taxes & fees
20 May - 21 May
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

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, (37 reviews)
"Everything was just perfect. Will be staying here again."
United States
Joshua L.
The price is NZ$412
includes taxes & fees
26 May - 27 May
Country home with beautiful views and access to hiking, biking, and horse trails

Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs

Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs
Floyd knobs
The price is NZ$435
includes taxes & fees
16 May - 17 May
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs

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, (20 reviews)
"Clean room, family friendly"
United States
Josh
The price is NZ$268
includes taxes & fees
21 May - 22 May
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

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, (4 reviews)
"Beautiful home & I would highly recommend staying there👍👍"
United States
Kenneth
The price is NZ$530
includes taxes & fees
18 May - 19 May
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

Lakeside Cottage Getaway on 50 Acres of Gardens

Lakeside Cottage Getaway on 50 Acres of Gardens
Henryville
The price is NZ$502
includes taxes & fees
28 May - 29 May
Lakeside Cottage Getaway on 50 Acres of Gardens

Emerald Lake Retreat Charlestown

Emerald Lake Retreat Charlestown
Charlestown
10.0 out of 10, Exceptional, (3 reviews)
"Roomy, clean, nice setting in nice neighborhood."
United States
David P.
The price is NZ$748
includes taxes & fees
19 May - 20 May
Emerald Lake Retreat Charlestown

Cozy motor home in Adorable Fredericksburg IN with all amenities inside and out!

Cozy motor home in Adorable Fredericksburg IN with all amenities inside and out!
Fredericksburg
10.0 out of 10, Exceptional, (1 review)
"Served its purpose for us! cozy, quiet & comfy! If I ever decide to revisit Indiana, I will stay here again!"
United States
Jeremy R.
The price is NZ$371
includes taxes & fees
2 June - 3 June
Cozy motor home in Adorable Fredericksburg IN with all amenities inside and out!

Lakeside Cabin: 4 bed/2.5 bath

Lakeside Cabin: 4 bed/2.5 bath
Henryville
4.0 out of 10, (1 review)
"The property upon arrival looks very impressive and beautiful but when entering the house many issues came up. The first thing that occurred was the inner storm door handle fell off immediately. Once inside it was clear that minimal cleaning had been done as the floors were not swept or mopped. The refrigerator had something spilled all over and dried to the shelves and had to be scrubbed to use it. The coffee station was well stocked but the machine did not function and we had to buy one for...
United States
Anonymous traveller
The price is NZ$1,022
includes taxes & fees
22 May - 23 May
Lakeside Cabin: 4 bed/2.5 bath
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 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$268 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?

35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.: This holiday home rental outside of South Boston offers a selection of games, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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.