South Boston Vacation Rentals from $158: Search Short-Term Rentals

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

Star Ridge | Private Estate | Sleeps 20 | Hot Tub : This vacation home rental near 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 you can cook with friends or family.

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Our top choices for South Boston vacation rentals

Coffee/tea maker, fridge, microwave, oven

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

Henryville

Forrest K.

$226 nightly

Aug 5 - Aug 6

Total with taxes and fees

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

Salem

Kenneth

$315 nightly

Aug 18 - Aug 19

Total with taxes and fees

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.

$253 nightly

Aug 9 - Aug 10

Total with taxes and fees

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

Henryville

Michael S.

5. Cozy Country Cabin quiet country retreat

Orleans

Pamela

$188 nightly

Aug 5 - Aug 6

Total with taxes and fees

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

Memphis

Lynn R.

$140 nightly

Aug 5 - Aug 6

Total with taxes and fees

7. Lakeside Cottage: 1 bed/1 bath

Henryville

Jonathan B.

$264 nightly

Aug 5 - Aug 6

Total with taxes and fees

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

Floyd knobs

Fr. Jay H.

$180 nightly

Aug 5 - Aug 6

Total with taxes and fees

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

Wood Township

martha u.

$1,497 nightly

Aug 5 - Aug 6

Total with taxes and fees

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.

$537 nightly

Aug 5 - Aug 6

Total with taxes and fees

11. Cozy Tiny House in Scottsburg

Scottsburg

Hipolito C.

$167 nightly

Aug 13 - Aug 14

Total with taxes and fees

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

Vallonia

Michael B.

$281 nightly

Aug 10 - Aug 11

Total with taxes and fees

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

Georgetown

Ralph P.

$311 nightly

Aug 5 - Aug 6

Total with taxes and fees

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Top South Boston Hotel Reviews

Days Inn & Suites by Wyndham Sellersburg

10/10 Excellent

"Sean helped us check in (we were extra late). He was helpful and kind and gave us the best room! Room was clean and fully stocked. Beds were extra comfy! AC worked well but was noisy. Breakfast: pancakes, cereal, oatmeal, coffee, milk, yogurt and fruit. Would absolutely stay here again."

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."

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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Boston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Boston vacation 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 low season months. For more hustle and bustle, you may prefer to visit South Boston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Boston rentals

At Expedia, we put the best South Boston vacation 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 vacation.

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 vacation rental in South Boston?

Yes, we give you a choice of vacation rentals close to well known sights in South Boston, or you can choose a more remote option if you're looking for a relaxing stay.

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

Star Ridge | Private Estate | Sleeps 20 | Hot Tub: This vacation home rental near 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 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 larger area.

What are vacation rentals like in South Boston?

Vacation rentals are private properties you can book for several days or more in South Boston. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.

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Check prices for these dates

Our top choices for South Boston vacation 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

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

7. Lakeside Cottage: 1 bed/1 bath

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

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

10. Lakeside Cabin: 4 bed/2.5 bath

11. Cozy Tiny House in Scottsburg

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

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

Find vacation rentals that suit your style

Top South Boston Hotel Reviews

Days Inn & Suites by Wyndham Sellersburg

HavenPointe Inn & Suites

Ramada by Wyndham Sellersburg/Louisville North

SureStay by Best Western Salem

Knights Inn and Suites Salem

Cozy Country Cabin quiet country retreat

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

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

Lakeside Cabin: 4 bed/2.5 bath

Find out more about South Boston

Frequently asked questions

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