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South Boston Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for South Boston holiday 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, (29 reviews)
"Great host and a great location!"
United States
P a.
The price is HK$777
HK$1,321 total
includes taxes & fees
29 Oct - 30 Oct
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
A brick building with a central entrance, a small porch, and a pathway leading to the entrance.

2. 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
9.6 out of 10, Exceptional, (10 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 HK$1,165
HK$2,500 total
includes taxes & fees
4 Nov - 5 Nov
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
A modern kitchen with white cabinets, a large island with bar stools, a built-in oven, and a stainless steel refrigerator.

3. 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)
"Loved the dog-friendly house that even had a nice small fenced in area. Super quiet and close to the Knobstone trail for some exploring. The house was easy to find and access and the host was friendly. Thanks for the great place to stay!"
United States
Forrest K.
The price is HK$1,295
HK$2,259 total
includes taxes & fees
31 Oct - 1 Nov
Country home with beautiful views and access to hiking, biking, and horse trails
A rustic cabin by a pond with a grassy area and trees in the background.

4. Cozy Country Cabin quiet country retreat

Cozy Country Cabin quiet country retreat
Orleans
10.0 out of 10, Exceptional, (217 reviews)
"Great quiet get away in the country Watch deer hummingbirds chipmunk from the porch Feed fish Bloomington not far for a steak dinner Spring mill park for hiking"
United States
Pamela
The price is HK$981
HK$1,620 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Country Cabin quiet country retreat
A room with a bed, two armchairs, a small table, and a microwave.

5. Lakeside Cottage: 1 bed/1 bath

Lakeside Cottage: 1 bed/1 bath
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 HK$1,096
HK$2,476 total
includes taxes & fees
25 Oct - 26 Oct
Lakeside Cottage: 1 bed/1 bath
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, (8 reviews)
"Great spot for a guys weekend."
United States
Fr. Jay H.
The price is HK$1,236
HK$1,601 total
includes taxes & fees
24 Oct - 25 Oct
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, (174 reviews)
"Great host, clean house in a great location. We really enjoyed our stay."
United States
Michael S.
The price is HK$1,576
HK$3,714 total
includes taxes & fees
27 Oct - 28 Oct
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 HK$1,636
HK$2,581 total
includes taxes & fees
24 Oct - 25 Oct
Quiet Forest Hideaway Near Fredericksburg
A modern kitchen with a central island, black cabinets, a microwave, and a stove.

9. 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 HK$1,723
HK$2,774 total
includes taxes & fees
31 Oct - 1 Nov
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
A large, multi-story wooden house with a dock extending over a body of water, surrounded by trees.

10. Lakeside Cabin: 4 bed/2.5 bath

Lakeside Cabin: 4 bed/2.5 bath
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 HK$2,601
HK$5,499 total
includes taxes & fees
3 Nov - 4 Nov
Lakeside Cabin: 4 bed/2.5 bath
A white bedroom with a large bed, a wooden nightstand, and a wall-mounted lamp.

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

Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden
Henryville
The price is HK$4,245
HK$9,307 total
includes taxes & fees
9 Nov - 10 Nov
Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden
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 HK$7,401
HK$15,022 total
includes taxes & fees
26 Oct - 27 Oct
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

Mariann Travel Inn Scottsburg

Mariann Travel Inn Scottsburg

8/10 Good
"My overnight at Mariann's Travel Inn was everything I needed: comfy bed, hot shower, clean room at a good price. I have stayed before and will stay again."
Anne 1-night trip
Posted 2 days ago
Mariann Travel Inn Scottsburg

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:

  • View our selection of featured holiday rentals in South Boston
  • Use the map to find apartments and other holiday homes in the South Boston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Boston while they last

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

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. Champions Pointe Golf Club and Huber’s Orchard, Winery & Vineyards 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.