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South Boston Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for South Boston vacation rentals

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

1. 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, (31 reviews)
"Great host and a great location!"
United States
P a.
The price is ￥16,627
￥26,841 total
includes taxes & fees
Dec 5 - Dec 6
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
A rustic cabin by a pond with a grassy area and trees in the background.

2. Cozy Country Cabin quiet country retreat

Cozy Country Cabin quiet country retreat
Orleans
10.0 out of 10, Exceptional, (217 reviews)
"Great place!"
United States
Joe C.
The price is ￥19,794
￥31,639 total
includes taxes & fees
Nov 19 - Nov 20
Cozy Country Cabin quiet country retreat
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

The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
Salem
9.8 out of 10, Exceptional, (11 reviews)
"We loved our stay here. It was the perfect location. The house was clean and I would stay here again."
United States
Nina L.
The price is ￥23,964
￥48,140 total
includes taxes & fees
Nov 10 - Nov 11
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
A room with a bed, two armchairs, a small table, and a microwave.

4. Tiny Lakeside Cottage I 50 Acres of Gardens

Tiny Lakeside Cottage I 50 Acres of Gardens
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 ￥22,141
￥47,851 total
includes taxes & fees
Nov 6 - Nov 7
Tiny Lakeside Cottage I 50 Acres of Gardens
A modern kitchen with white cabinets, a large island with bar stools, a built-in oven, and a stainless steel refrigerator.

5. 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, (44 reviews)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
The price is ￥26,128
￥43,451 total
includes taxes & fees
Nov 11 - Nov 12
Country home with beautiful views and access to hiking, biking, and horse trails
A rustic cabin interior with a stone fireplace, wooden beams, a green sofa, and a television.

6. 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
9.0 out of 10, Wonderful, (10 reviews)
"Great spot for a guys weekend."
United States
Fr. Jay H.
The price is ￥24,962
￥30,715 total
includes taxes & fees
Nov 6 - Nov 7
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs
A rustic cabin with a porch, stone walls, and an American flag.

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

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Henryville
10.0 out of 10, Exceptional, (176 reviews)
"Great host, clean house in a great location. We really enjoyed our stay."
United States
Michael S.
The price is ￥33,220
￥76,760 total
includes taxes & fees
Nov 11 - Nov 12
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
A cozy living room with a brown sofa, a small side table with a lamp, a potted plant, and a patterned rug.

8. Quiet Forest Hideaway Near Fredericksburg

Quiet Forest Hideaway Near Fredericksburg
Fredericksburg
9.0 out of 10, Wonderful, (2 reviews)
The price is ￥36,716
￥53,497 total
includes taxes & fees
Nov 19 - Nov 20
Quiet Forest Hideaway Near Fredericksburg
A large, multi-story wooden house with a dock extending over a body of water, surrounded by trees.

9. Enchanting Lakeside Cabin I 50 Acres of Gardens

Enchanting Lakeside Cabin I 50 Acres of Gardens
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 ￥56,158
￥105,447 total
includes taxes & fees
Nov 16 - Nov 17
Enchanting Lakeside Cabin I 50 Acres of Gardens
A modern kitchen with a central island, black cabinets, a microwave, and a stove.

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, (19 reviews)
"Outstanding place to stay. Plenty of peace and quiet but still not too far from groceries and gas."
United States
James
The price is ￥34,837
￥51,432 total
includes taxes & fees
Dec 1 - Dec 2
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
A spacious living area with a stone fireplace, leather furniture, and a wooden staircase.

11. The Secluded Woodland Retreat | Cabin + Cottage

The Secluded Woodland Retreat | Cabin + Cottage
Henryville
The price is ￥81,721
￥173,767 total
includes taxes & fees
Dec 2 - Dec 3
The Secluded Woodland Retreat | Cabin + Cottage
A large house with a covered patio area featuring outdoor seating and a fire pit.

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 ￥149,351
￥287,396 total
includes taxes & fees
Nov 9 - Nov 10
Star Ridge | Private Estate | Sleeps 20 | Hot Tub
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

Ramada by Wyndham Sellersburg/Louisville North

Ramada by Wyndham Sellersburg/Louisville North

10/10 Excellent
"We had a great clean room, and the HCP bathroom was perfect! Good location also. Breakfast was top-notch."
Danny 1-night trip
Posted 1 day ago
Ramada by Wyndham Sellersburg/Louisville North

Find out more about South Boston

Search for holiday rentals in South Boston on Expedia! You can easily find your home rentals, villas, holiday apartments in South Boston using one of the methods below:

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Look no further and take a look at our great range of rental properties in South Boston!

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.