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South Boston Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for South Boston vacation rentals

Property grounds

Cozy Country Cabin quiet country retreat

Cozy Country Cabin quiet country retreat
Orleans
10.0 out of 10, Exceptional, (201 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 ￥23,395
￥36,996 total
includes taxes & fees
Jul 11 - Jul 12
Cozy Country Cabin quiet country retreat
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, (38 reviews)
"Everything was just perfect. Will be staying here again."
United States
Joshua L.
The price is ￥23,796
￥40,472 total
includes taxes & fees
Jun 17 - Jun 18
Country home with beautiful views and access to hiking, biking, and horse trails
Fridge, microwave, oven, stovetop

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
The price is ￥25,238
￥32,684 total
includes taxes & fees
Jun 19 - Jun 20
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs
Interior

Emerald Lake Retreat Charlestown

Emerald Lake Retreat Charlestown
Charlestown
10.0 out of 10, Exceptional, (3 reviews)
"Roomy, clean, nice setting in nice neighborhood."
United States
David P.
Emerald Lake Retreat Charlestown
Exterior

Moonlit Cottage Near Louisville

Moonlit Cottage Near Louisville
Palmyra
6.0 out of 10, (1 review)
"Beautiful land and venue with great location! Absolutely loved those aspects and would’ve given it more stars if there were no concerns. The only issues we had were regarding cleanliness (a very strong mold smell resulting from a kitchen sink leak in the cabinet below) and pest infestations in the kitchen. Both were communicated to the property manager who advised they relayed them to the owners. We made it work as we weren’t at the house much at all, but it would have been very nice to receive...
United Kingdom
Stephanie C.
The price is ￥12,258
￥45,267 total
includes taxes & fees
Jun 16 - Jun 17
Moonlit Cottage Near Louisville
Exterior

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, (165 reviews)
"Great place to stay and feel right at. Home. "
United States
Adam D.
The price is ￥64,096
￥113,894 total
includes taxes & fees
Jul 14 - Jul 15
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
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
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home & I would highly recommend staying there👍👍"
United States
Kenneth
The price is ￥25,238
￥51,958 total
includes taxes & fees
Jun 17 - Jun 18
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
1 bedroom, free WiFi, bed sheets

Lakeside Cottage: 1 bed/1 bath

Lakeside Cottage: 1 bed/1 bath
Henryville
The price is ￥20,623
￥48,671 total
includes taxes & fees
Jun 16 - Jun 17
Lakeside Cottage: 1 bed/1 bath
Fridge, microwave, oven, stovetop

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, (16 reviews)
"This place was great. We will be staying here if ever back in the area. "
United States
Michael B.
The price is ￥29,564
￥49,445 total
includes taxes & fees
Jun 22 - Jun 23
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
Smart TV

Cozy motor home in Adorable Fredericksburg IN with all amenities inside and out!

Cozy motor home in Adorable Fredericksburg IN with all amenities inside and out!
Fredericksburg
10.0 out of 10, Exceptional, (1 review)
"Served its purpose for us! cozy, quiet & comfy! If I ever decide to revisit Indiana, I will stay here again!"
United States
Jeremy R.
The price is ￥15,223
￥34,099 total
includes taxes & fees
Jun 17 - Jun 18
Cozy motor home in Adorable Fredericksburg IN with all amenities inside and out!
Dining

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

Hope Hill Hideaway - Family Country Retreat in Southern Indiana near Louisville
Georgetown
10.0 out of 10, Exceptional, (1 review)
"The stay was amazing. We had some issues with the booking, not at all the hosts fault, it was a technical issues and jenni and wyatt were so helpful and stayed in full contact till it was sorted. The property was so cozy and if we were there for a longer stay we would have loved to use the fire pit and hang out in the beautiful natural scenery. We only stayed for two nights and kept busy the entire time but it will definitely be a repeat to stay at the property. Everything was clean....
United States
Nicholas K.
The price is ￥28,843
￥56,494 total
includes taxes & fees
Jul 1 - Jul 2
Hope Hill Hideaway - Family Country Retreat in Southern Indiana near Louisville
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, (23 reviews)
"Very nice stay!"
United States
Tammy W.
The price is ￥15,223
￥25,350 total
includes taxes & fees
Jun 22 - Jun 23
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
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

Knights Inn and Suites Salem

Knights Inn and Suites Salem

8/10 Good
"Room was very big and had a separate seating area which was very nice. It looked very clean however had an unpleasant odor that we thought was just from being closed up but didn't go away after leaving door open fir a bit and running air-conditioner. The tub drained extremely slow so had to stand in ankle deep water while showering. Other than those 2 things, it was a nice, clean, roomy and affordable property."
Debby 1-night trip
Posted 16 hours ago
Knights Inn and Suites Salem

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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  • 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 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?

35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.: This vacation home rental near South Boston offers a selection of games, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, 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.