South Boston Vacation Rentals

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Our top choices for South Boston vacation rentals

Cozy Country Cabin quiet country retreat

Cozy Country Cabin quiet country retreat
Orleans
10.0 out of 10, Exceptional, (197 reviews)
"Fireplace was cozy Nice shower Comfortable furniture "
United States
James
The price is CA $153
CA $262 total
includes taxes & fees
May 7 - May 8
Cozy Country Cabin quiet country retreat

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, (161 reviews)
"We had a great time during our stay. The cabin was as advertised and we were able to get some great family time together. "
United States
Amy M.
The price is CA $428
CA $812 total
includes taxes & fees
May 7 - May 8
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

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, (36 reviews)
"Everything was just perfect. Will be staying here again."
United States
Joshua L.
The price is CA $202
CA $344 total
includes taxes & fees
May 10 - May 11
Country home with beautiful views and access to hiking, biking, and horse trails

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, (14 reviews)
"This place was great. We will be staying here if ever back in the area. "
United States
Michael B.
The price is CA $238
CA $406 total
includes taxes & fees
May 10 - May 11
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

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 CA $203
CA $433 total
includes taxes & fees
May 11 - May 12
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

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 CA $281
CA $352 total
includes taxes & fees
May 6 - May 7
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs

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.
The price is CA $177
CA $647 total
includes taxes & fees
May 10 - May 11
Emerald Lake Retreat Charlestown

Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (7 reviews)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is CA $112
CA $240 total
includes taxes & fees
May 6 - May 7
Cozy Tiny House in Scottsburg

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, (19 reviews)
"Clean room, family friendly"
United States
Josh
The price is CA $129
CA $216 total
includes taxes & fees
May 13 - May 14
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

Lakeside Cottage Getaway on 50 Acres of Gardens

Lakeside Cottage Getaway on 50 Acres of Gardens
Henryville
The price is CA $167
CA $402 total
includes taxes & fees
May 7 - May 8
Lakeside Cottage Getaway on 50 Acres of Gardens

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 CA $104
CA $391 total
includes taxes & fees
May 6 - May 7
Moonlit Cottage Near Louisville

Lakeside Cabin: 4 bed/2.5 bath

Lakeside Cabin: 4 bed/2.5 bath
Henryville
4.0 out of 10, (1 review)
"The property upon arrival looks very impressive and beautiful but when entering the house many issues came up. The first thing that occurred was the inner storm door handle fell off immediately. Once inside it was clear that minimal cleaning had been done as the floors were not swept or mopped. The refrigerator had something spilled all over and dried to the shelves and had to be scrubbed to use it. The coffee station was well stocked but the machine did not function and we had to buy one for...
United States
Anonymous traveller
The price is CA $367
CA $838 total
includes taxes & fees
May 10 - May 11
Lakeside Cabin: 4 bed/2.5 bath
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

Find out more about South Boston

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with South Boston. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 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.