South Boston Vacation Rentals from AED 581: 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

A covered patio with a door, two wicker chairs, and string lights.

1. Cozy Tiny House in Scottsburg

Scottsburg

Hipolito C.

AED 753 total

includes taxes & fees

24 Oct - 25 Oct

A compact kitchen with a refrigerator, microwave, stove, and sink. There is a dining table with chairs and a patterned rug.

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

Memphis

P a.

AED 581 total

includes taxes & fees

2 Nov - 3 Nov

A brick building with a central entrance, a small porch, and a pathway leading to the entrance.

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

Salem

Andrew H.

AED 1,284 total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with white cabinets, a large island with bar stools, a built-in oven, and a stainless steel refrigerator.

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

Henryville

Forrest K.

AED 1,053 total

includes taxes & fees

2 Nov - 3 Nov

A rustic cabin by a pond with a grassy area and trees in the background.

5. Cozy Country Cabin quiet country retreat

Orleans

Pamela

AED 758 total

includes taxes & fees

22 Oct - 23 Oct

A room with a bed, two armchairs, a small table, and a microwave.

6. Lakeside Cottage: 1 bed/1 bath

Henryville

Jonathan B.

AED 1,131 total

includes taxes & fees

5 Oct - 6 Oct

A rustic cabin interior with a stone fireplace, wooden beams, a green sofa, and a television.

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

Floyd knobs

David

AED 749 total

includes taxes & fees

10 Oct - 11 Oct

A rustic cabin with a porch, stone walls, and an American flag.

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

Henryville

Michael S.

AED 1,758 total

includes taxes & fees

5 Oct - 6 Oct

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Top South Boston Hotel Reviews

HavenPointe Inn & Suites

10/10 Excellent

"The shower could use handrails as the floor seemed slick. We put a towel down on the shower floor and everything was fine."

Days Inn & Suites by Wyndham Sellersburg

10/10 Excellent

"Property was easy to get to off of the highway and it was nice and quiet. It is nice it is located right beside Cracker Barrel. I want to stay as soon as we walked in we felt welcome and comfortable the staff was amazing! Definitely a family owned/ran business as we first met son the father and the grandfather sitting in the laundry room that would just send a text when his son was needed at the front desk. They were all so nice and gave us some good tips on what to do throughout the area! Would definitely stay here again when we come back to Louisville!"

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

10/10 Excellent

"Wonderful getaway spot, hope to come back in Fall. Stairs definitely not for toddlers, elderly, or dogs (ours could get up easy but had to make her let us carry her down) and require caution for anyone but we just blocked off and managed fine"

The Destination B&B

10/10 Excellent

"Fantastic B and B. Super comfortable, spotlessly clean, great breakfast and the setting is on a farm in the bucolic countryside. Also on the property is a cafe, antique store, and wedding or celebration venue. The owners are incredibly personable, kind, and very knowledgeable about the area. It’s a perfect place for a group, a romantic getaway for 2, a girls weekend, a family reunion… or if you are passing through and need a restful night. We have stayed twice at The Destination and I look forward to stays in the future."

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."

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. Champions Pointe Golf Club and Huber’s Orchard, Winery & Vineyards 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. Cozy Tiny House in Scottsburg

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

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

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

5. Cozy Country Cabin quiet country retreat

6. Lakeside Cottage: 1 bed/1 bath

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

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

9. Quiet Forest Hideaway Near Fredericksburg

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

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

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

Find vacation rentals that suit your style

Top South Boston Hotel Reviews

HavenPointe Inn & Suites

Cozy Country Cabin quiet country retreat

SureStay by Best Western Salem

Days Inn & Suites by Wyndham Sellersburg

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

The Destination B&B

Cozy Tiny House in Scottsburg

Lakeside Cabin: 4 bed/2.5 bath

Star Ridge | Private Estate | Sleeps 20 | Hot Tub

Frequently asked questions

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