South Boston Holiday Rentals from €141: Search Short-Term Rentals

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

Star Ridge | Private Estate | Sleeps 20 | Hot Tub : This holiday home rental outside of South Boston is located in the mountains, and has a balcony, a pool table and air conditioning to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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Our top choices for South Boston holiday rentals

Coffee/tea maker, fridge, microwave, oven

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

Henryville

Forrest K.

includes taxes & fees

5 Aug - 6 Aug

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

Salem

Kenneth

includes taxes & fees

17 Aug - 18 Aug

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

New Pekin

"This place is a hidden gem!!! The pictures do not do it justice, it is stunning! It’s very clean and they have everything you could need! The owners were so kind and communicated well!!! The porch is extremely nice! I sat there most of the time and drank my coffee in the mornings! You are surrounded by woods and nature. There is a fire pit available for use and the wood is provided for you! Make sure to bring shampoo and conditioner. And a fan or sound machine at night if you need sound to...

Courtney Q.

includes taxes & fees

9 Aug - 10 Aug

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

Henryville

Michael S.

includes taxes & fees

4 Aug - 5 Aug

5. Cozy Country Cabin quiet country retreat

Orleans

Pamela

includes taxes & fees

5 Aug - 6 Aug

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

Memphis

Lynn R.

includes taxes & fees

4 Aug - 5 Aug

7. Lakeside Cottage: 1 bed/1 bath

Henryville

Jonathan B.

includes taxes & fees

4 Aug - 5 Aug

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

Floyd knobs

Fr. Jay H.

includes taxes & fees

5 Aug - 6 Aug

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

Wood Township

martha u.

includes taxes & fees

4 Aug - 5 Aug

10. Lakeside Cabin: 4 bed/2.5 bath

Henryville

"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!!"

Melanie G.

includes taxes & fees

5 Aug - 6 Aug

11. Cozy Tiny House in Scottsburg

Scottsburg

Hipolito C.

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

Vallonia

Michael B.

includes taxes & fees

10 Aug - 11 Aug

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

Georgetown

Ralph P.

includes taxes & fees

5 Aug - 6 Aug

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Top South Boston Hotel Reviews

Ramada by Wyndham Sellersburg/Louisville North

10/10 Excellent

"Everything was great. All the normal things. Good size breakfast area. Would stay there again if in the area."

SureStay by Best Western Salem

10/10 Excellent

"Grounds and Motel well kept. Our room was going through renovations, but clean. Was missing the baseboard . Bed was comfortable . Breakfast provided was beyond expectations with Sausage, Eggs and Waffles along with an offering of Muffins, Danish and fruits. Would stay here again."

Cozy Country Cabin quiet country retreat

10/10 Excellent

"We absolutely loved it. We had to little toads (Alfred and Albert) come sit with us on the porch when we were just decompressing and looking at the stars. I would love to go back out there and I hopefully will. I live in the city and have 7 kids so getting away from all of that with just me and my wife was definitely needed."

Days Inn & Suites by Wyndham Sellersburg

10/10 Excellent

"In all fairness I only saw the night clerk when I checked in about 1 in the morning and very tired from driving and the morning clerk when I checked out, but both were very nice. The room though out dated was spacious clean, and comfortable. I liked that the counter with the sink was not in the bathroom but next to the refrigerator which was an apartment size instead of a mini one. The bathroom was a decent size room."

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

10/10 Excellent

"The house was spacious and comfortable. We had a great time using the game room and hot tub. The house felt tucked away, but was very accessible to local towns and the interstate. April was a great host and easy to communicate with. For things to do, would recommend Lake Hardy's beach, Soar n Bounce in Clarksville, and a stop at Java Station 31 for coffee."

Lakeside Cabin: 4 bed/2.5 bath

10/10 Excellent

"Overall, this is a really nice and peaceful, cabin. They provide everything you need so you don’t have to rush to the grocery store right when you get there which is so nice. However, the only thing was the downstairs basement has a really loud buzzing noise due to electricity box.. if you’re a person sensitive to sound, it would be really hard to sleep down there."

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 €141 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?

Star Ridge | Private Estate | Sleeps 20 | Hot Tub: This holiday home rental outside of South Boston is located in the mountains, and has a balcony, a pool table and air conditioning to put you at ease in your new surroundings. It has 9 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. Virginia Pine Chestnut Oak Nature Preserve and Champions Pointe Golf Club 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.

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Check prices for these dates

Our top choices for South Boston holiday rentals

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

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

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

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

5. Cozy Country Cabin quiet country retreat