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, (188)
"We really enjoyed our stay. The cabin is very nice and so is the pond."
United States
Scott H.
$173 nightly
The price is $191
Dec 11 - Dec 12
Total with taxes and fees
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, (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.
$423 nightly
The price is $478
Dec 11 - Dec 12
Total with taxes and fees
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Large Group Rental Near Louisville with Mountain Views

Large Group Rental Near Louisville with Mountain Views
Wood Township
10.0 out of 10, Exceptional, (6)
"Great location and stunning views!!"
United States
Jeff R.
Large Group Rental Near Louisville with Mountain Views

Cozy Cabin Escape in Borden, IN – Minutes from Louisville & Outdoor Trails

Cozy Cabin Escape in Borden, IN – Minutes from Louisville & Outdoor Trails
2.0 star property
Borden
Cozy Cabin Escape in Borden, IN – Minutes from Louisville & Outdoor Trails

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.
$140 nightly
The price is $158
Dec 15 - Dec 16
Total with taxes and fees
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (4)
"Wonderful accommodations. Comfortable and clean. We enjoyed our stay. I am sure we will return as Hope was a great host."
United States
Karen P.
$154 nightly
The price is $172
Dec 29 - Dec 30
Total with taxes and fees
Cozy Tiny House in Scottsburg

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.
$225 nightly
The price is $251
Dec 12 - Dec 13
Total with taxes and fees
Country home with beautiful views and access to hiking, biking, and horse trails

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.
$399 nightly
The price is $451
Dec 12 - Dec 13
Total with taxes and fees
Emerald Lake Retreat Charlestown

5 BR, 4 baths, Pool, HotTub, Family Friendly, near Louisville KY, Private

5 BR, 4 baths, Pool, HotTub, Family Friendly, near Louisville KY, Private
Fredericksburg
10.0 out of 10, Exceptional, (118)
"Beautiful place inside and out. Totally loved the stay. "
United States
Tonda A.
5 BR, 4 baths, Pool, HotTub, Family Friendly, near Louisville KY, Private

2600 SF home 15 Minutes from Downtown Louisville in New Albany. Full basement.

2600 SF home 15 Minutes from Downtown Louisville in New Albany. Full basement.
New Albany
9.4 out of 10, Exceptional, (10)
"It was a fast stay but super nice and accommodating!"
United States
Rachel P.
2600 SF home 15 Minutes from Downtown Louisville in New Albany. Full basement.

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
$266 nightly
The price is $297
Dec 11 - Dec 12
Total with taxes and fees
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.

35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.
Fredericksburg
9.6 out of 10, Exceptional, (20)
"Excellent place very nice "
United States
Donna G.
35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.

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
$334 nightly
The price is $352
Dec 31 - Jan 1, 2026
Total with taxes and fees
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

Relaxing Country Getaway

Relaxing Country Getaway
Lexington
9.4 out of 10, Exceptional, (43)
"Very nice. We enjoyed ourselves a lot and would come back! "
United States
Stephanie G.
Relaxing Country Getaway

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.
$536 nightly
The price is $600
Dec 11 - Dec 12
Total with taxes and fees
Tell your family to meet you here!<br>No Drinking Parties

3BR/3BA Peaceful Retreat - Fire pit & Game room

3BR/3BA Peaceful Retreat - Fire pit & Game room
Vallonia
3BR/3BA Peaceful Retreat - Fire pit & Game room

Moonlit Cottage Near Louisville

Moonlit Cottage Near Louisville
Palmyra
6.0 out of 10, (1)
"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.
$230 nightly
The price is $255
Dec 15 - Dec 16
Total with taxes and fees
Moonlit Cottage Near Louisville

Anjuna River House - the hidden Scandi cabin on 12 acres in Southern Indiana!

Anjuna River House - the hidden Scandi cabin on 12 acres in Southern Indiana!
New Pekin
10.0 out of 10, Exceptional, (8)
"Property was very unique to Indiana. Only a couple hours from Indy made it perfect for a weekend getaway. The property was awesome, owners were great to work with, and just an overall good experience. Highly recommend!"
United States
Kolten C.
Anjuna River House - the hidden Scandi cabin on 12 acres in Southern Indiana!

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
$296 nightly
The price is $332
Dec 16 - Dec 17
Total with taxes and fees
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

Stonecrest 722, Modern 2Bd Apt I Parking I Gym

Stonecrest 722, Modern 2Bd Apt I Parking I Gym
New Albany
Stonecrest 722, Modern 2Bd Apt I Parking I Gym
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

Everything you need to know about South Boston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Boston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Boston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Boston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Boston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Boston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Boston rentals

At Expedia, we put the best South Boston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Boston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Boston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Boston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.