South Boston Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Vacation Rentals in South Boston

Property grounds
Cozy Country Cabin quiet country retreat

Cozy Country Cabin quiet country retreat

Orleans
10.0 out of 10, Exceptional, (186)
"We really enjoyed our stay. The cabin is very nice and so is the pond."
United States
Scott H.
The price is ￥17,475
￥29,743 total
includes taxes & fees
Dec 9 - Dec 10
Cozy Country Cabin quiet country retreat
Fridge, microwave, oven, stovetop
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, (13)
"Property was very clean, smelt great, and spacious. Located in a nice neighborhood. Hosts were extremely accommodating and friendly. Would definitely stay here again if I'm back in the area for an overnight trip. "
United States
Mandy M.
The price is ￥14,756
￥24,573 total
includes taxes & fees
Dec 9 - Dec 10
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
Exterior
Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg

Scottsburg
9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is ￥12,271
￥26,791 total
includes taxes & fees
Dec 29 - Dec 30
Cozy Tiny House in Scottsburg
Exterior detail
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

4.0 star property
Sellersburg
9.4 out of 10, Exceptional, (10)
"Very nice house in a nice neighborhood, spacious home environmental, felt more that at home there,"
United States
Tammy
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb
Fridge, microwave, oven, stovetop
Emerald Lake Retreat Charlestown

Emerald Lake Retreat Charlestown

Charlestown
10.0 out of 10, Exceptional, (3)
"This a great place for families to gather. It's very spacious and clean and comfortable. And though it's in a quiet and peaceful area with a small lake at the base of the property, places to eat and get groceries are just a short drive away. There's a wonderful seating area around a firepit, too!"
United States
Kelly P.
The price is ￥18,640
￥71,087 total
includes taxes & fees
Dec 12 - Dec 13
Emerald Lake Retreat Charlestown
Fridge, microwave, oven, stovetop
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
10.0 out of 10, Exceptional, (28)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
The price is ￥23,067
￥38,536 total
includes taxes & fees
Dec 10 - Dec 11
Country home with beautiful views and access to hiking, biking, and horse trails
Smart TV, fireplace, video games, DVD player
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, (153)
"This is beautiful property and thoughtful amenities. The host is super responsive. We cannot wait to plan our next stay. "
United States
Katie A.
The price is ￥34,949
￥74,246 total
includes taxes & fees
Dec 11 - Dec 12
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Smart TV
Charming 2-bedroom cottage with WiFi, AC in wonderful New Pekin

Charming 2-bedroom cottage with WiFi, AC in wonderful New Pekin

New Pekin
The price is ￥31,454
￥73,155 total
includes taxes & fees
Dec 10 - Dec 11
Charming 2-bedroom cottage with WiFi, AC in wonderful New Pekin
Exterior
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

2.0 star property
Vallonia
10.0 out of 10, Exceptional, (13)
"Excellent place to stay. Everything was absolutely amazing. "
United States
Jimmy
The price is ￥27,260
￥46,190 total
includes taxes & fees
Dec 9 - Dec 10
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
Property grounds
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
"This is a lovingly restored historical property with many beautiful original features, like the staircase & railings. The little town is so nice, and the people are friendly. We came down from Georgia to help a family member move into the home they just bought and needed a comfortable place to stay after moving stuff all day. We all decided we need to come for a longer time so we can check out all the interesting historical site nearby. We ate out every day & only used the coffee maker but the...
United States
Elizabeth
The price is ￥24,884
￥51,703 total
includes taxes & fees
Dec 9 - Dec 10
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
Exterior
Tell your family to meet you here!<br>No Drinking Parties

Tell your family to meet you here!<br>No Drinking Parties

Hardinsburg
10.0 out of 10, Exceptional, (37)
"We love staying here for our annual Kayak trip!"
United States
Joni D.
The price is ￥41,799
￥93,266 total
includes taxes & fees
Dec 9 - Dec 10
Tell your family to meet you here!<br>No Drinking Parties
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
"Clean room, helpful staff, good breakfast "
Jessica 1-night trip
Posted 5 days 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?

Cozy Tiny House in Scottsburg: This vacation home rental near South Boston has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.