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Our top choices for South Boston holiday rentals

1. Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (8 reviews)
"Great location nice place comfortable "
United States
Hipolito C.
The price is £133
includes taxes & fees
19 Aug - 20 Aug
Cozy Tiny House in Scottsburg

2. 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
9.8 out of 10, Exceptional, (42 reviews)
"Loved the dog-friendly house that even had a nice small fenced in area. Super quiet and close to the Knobstone trail for some exploring. The house was easy to find and access and the host was friendly. Thanks for the great place to stay!"
United States
Forrest K.
The price is £185
includes taxes & fees
27 Aug - 28 Aug
Country home with beautiful views and access to hiking, biking, and horse trails

3. 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
9.6 out of 10, Exceptional, (9 reviews)
"Beautiful home & I would highly recommend staying there👍👍"
United States
Kenneth
The price is £250
includes taxes & fees
25 Aug - 26 Aug
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

4. 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, (26 reviews)
"I can't say enough googd things about this Vrbo! CLEAN, great communication, great instructions on finding the place. My short stay showed the owners to be so nice. "
United States
Lynn R.
The price is £120
includes taxes & fees
20 Aug - 21 Aug
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

5. Whispering Pines is a lovely 3-bedroom family-friendly home in a wooded setting.

Whispering Pines is a lovely 3-bedroom family-friendly home in a wooded setting.
New Pekin
10.0 out of 10, Exceptional, (3 reviews)
"Spotless, like new clean that felt like we were the first people to ever stay there. It was in a beautiful country setting and had comfortable furniture. They went above and beyond with stocked kitchen that made our stay so easy. Highly recommend and will likely stay again!"
United States
Trisha F.
The price is £205
includes taxes & fees
20 Aug - 21 Aug
Whispering Pines is a lovely 3-bedroom family-friendly home in a wooded setting.

6. Lakeside Cottage: 1 bed/1 bath

Lakeside Cottage: 1 bed/1 bath
Henryville
10.0 out of 10, Exceptional, (1 review)
"Awesome place in a gated property. The tiny home is exactly as pictured. Will 100% stay here again for future Henryville visits to see family."
United States
Jonathan B.
The price is £223
includes taxes & fees
19 Aug - 20 Aug
Lakeside Cottage: 1 bed/1 bath

7. Cozy Country Cabin quiet country retreat

Cozy Country Cabin quiet country retreat
Orleans
10.0 out of 10, Exceptional, (208 reviews)
"Great quiet get away in the country Watch deer hummingbirds chipmunk from the porch Feed fish Bloomington not far for a steak dinner Spring mill park for hiking"
United States
Pamela
The price is £157
includes taxes & fees
23 Aug - 24 Aug
Cozy Country Cabin quiet country retreat

8. 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
10.0 out of 10, Exceptional, (3 reviews)
"Great spot for a guys weekend."
United States
Fr. Jay H.
The price is £151
includes taxes & fees
19 Aug - 20 Aug
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs

9. Hope Hill Hideaway - Family Country Retreat in Southern Indiana near Louisville

Hope Hill Hideaway - Family Country Retreat in Southern Indiana near Louisville
Georgetown
10.0 out of 10, Exceptional, (3 reviews)
"We loved the country setting and the sounds of nature! Very nice home with all the amenities you need. Furniture was fresh and in great and comfortable condition parking and access was as easy as could be and the location was close to everything you need! Would love to stay there again!"
United States
Ralph P.
The price is £252
includes taxes & fees
19 Aug - 20 Aug
Hope Hill Hideaway - Family Country Retreat in Southern Indiana near Louisville

10. 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, (17 reviews)
"This place was great. We will be staying here if ever back in the area. "
United States
Michael B.
The price is £229
includes taxes & fees
19 Aug - 20 Aug
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

11. Lakeside Cabin: 4 bed/2.5 bath

Lakeside Cabin: 4 bed/2.5 bath
Henryville
8.0 out of 10, Very good, (3 reviews)
"The most beautiful and peaceful place we have ever stayed!! It was neat to find out the history and if you have the chance to stay here, DO NOT MISS IT!! if I could have stayed forever I would have. I was sad to leave! Just a very special place!! I’ve stayed in a LOT of different places and none compares!! It was an honor & our dogs absolutely loved the place!! Never seen them so happy and comfortable in a place!!"
United States
Melanie G.
The price is £450
includes taxes & fees
19 Aug - 20 Aug
Lakeside Cabin: 4 bed/2.5 bath

12. Star Ridge | Private Estate | Sleeps 20 | Hot Tub

Star Ridge | Private Estate | Sleeps 20 | Hot Tub
Wood Township
10.0 out of 10, Exceptional, (8 reviews)
"Really great to have our annual family reunion here for the second time! Such a great place for multigenerational fun! John is a wonderful host!"
United States
martha u.
The price is £1,161
includes taxes & fees
24 Aug - 25 Aug
Star Ridge | Private Estate | Sleeps 20 | Hot Tub

13. Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden

Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden
Henryville
The price is £824
includes taxes & fees
31 Aug - 1 Sept
Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden
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, 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 £120 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?

Country home with beautiful views and access to hiking, biking, and horse trails: This holiday home rental outside of South Boston is located in a rural location, and offers a selection of games, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, 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.