South Boston Vacation Rentals from ￥24,888: 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.

￥39,910 total

includes taxes & fees

Aug 12 - Aug 13

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

Salem

Kenneth

￥56,489 total

includes taxes & fees

Aug 17 - Aug 18

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.

￥44,578 total

includes taxes & fees

Aug 10 - Aug 11

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

￥32,480 total

includes taxes & fees

Aug 25 - Aug 26

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

Memphis

Lynn R.

￥24,888 total

includes taxes & fees

Aug 17 - Aug 18

7. Lakeside Cottage: 1 bed/1 bath

Henryville

Jonathan B.

￥48,440 total

includes taxes & fees

Aug 12 - Aug 13

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

Floyd knobs

Fr. Jay H.

￥31,911 total

includes taxes & fees

Aug 9 - Aug 10

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

Wood Township

martha u.

￥253,859 total

includes taxes & fees

Aug 16 - Aug 17

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.

￥98,438 total

includes taxes & fees

Aug 5 - Aug 6

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.

￥49,511 total

includes taxes & fees

Aug 10 - Aug 11

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

Georgetown

Ralph P.

￥55,268 total

includes taxes & fees

Aug 5 - Aug 6

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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

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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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