South Boston Holiday Rentals from €138: Search Short-Term Rentals

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Holiday Rentals in South Boston

"We very much enjoyed our stay at this cabin. "

includes taxes & fees

2 Jul - 3 Jul

Smart TV, fireplace, video games, DVD player

"Our family had a spectacular stay at the Stone Creek. Our kids (7, 3, 2 yo) had a blast playing pingpong, board games, and hot tub. Place was clean and we felt home. We’ll definitely come back!"

includes taxes & fees

5 Jul - 6 Jul

"Loved this property!!! We would definitely stay again!"

"Was the perfect little overnight stay! "

includes taxes & fees

2 Jul - 3 Jul

"Excellent communication, fast responses, very accommodating. The layout is fantastic with lots of open space, comfortable bedrooms, and excellent amenities. The backyard is absolutely huge, probably 3 acres or so. Would stay again for sure."

"We enjoyed staying there! Beautiful and cozy house, we loved the Christmas tree because we booked this house for New Year! It was really nice!"

"We stayed here for a basketball tournament at the KY Expo Center. Just a short drive away this location got us out of the hustle and bustle of downtown but was super easy to drive to our games each day. House was super cute, clean and had everything we needed!"

"What a beautiful spot! Secluded and wooded. Cozy and the hot tub hit the spot! 10 out of 10 would recommend. "

"Everything was great. Great communication and check in."

"Great location and stunning views!!"

includes taxes & fees

2 Jul - 3 Jul

"My friends and I had a great experience staying here. The large kitchen and dining room was perfect for us! Our bedrooms were very nice and the house was very clean! Great place to stay!"

includes taxes & fees

30 Jul - 31 Jul

"Wonderful Host and property."

"We needed a place to stay halfway-ish between Tennessee and Chicago, and this was a nice, clean place that totally fulfilled our needs."

"We really enjoyed the house. It’s very modern and beautifully decorated. We enjoyed both the inside and outside Definitely a great place for a quiet retreat."

"Excellent place very nice "

"Very nice house in a nice neighborhood, spacious home environmental, felt more that at home there,"

includes taxes & fees

14 Jul - 15 Jul

"This apartment was very conveniently located in New Albany and the 2 bedroom/2 bath suited our needs quite well. It was wonderful having a washer and dryer in the unit. However, the unit is on the third floor and my 93 year old mother had a very difficult time with the stairs. Had this detail been mentioned in the listing, I would have continued my search and looked for a ground floor rental. The unit is sparsely outfitted, which is understandable, so be prepared to go shopping for supplies when...

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Find out more about South Boston

Everything you need to know about South Boston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Boston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Boston holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Boston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Boston holiday rentals we have selected for you start as low as €138 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Boston rentals

At Expedia, we put the best South Boston holiday 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 holiday.

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.

Recent reviews of South Boston properties

Holiday Inn Express & Suites Scottsburg by IHG

5/5 Excellent

"Everything was great! They have a wonderful breakfast selection in morning also. "

A verified traveller stayed at Holiday Inn Express & Suites Scottsburg by IHG

Posted 4 days ago

5/5 Excellent

"If you come to this property expecting a $100 per night suite this property will exceed any reasonable expectations you had. If you want to compare it to hotels that cost double the price, there are minor things to nitpick, but I sent a picture of my room to a friend and told her guess which chain I'm staying in and she guessed Hilton."

A verified traveller stayed at Knights Inn and Suites Salem

Posted 5 days ago

5/5 Excellent

"The Destination B and B is a beautiful and interesting place. My favorite part of the house is the large front porch which has rocking chairs and a swing. I loved sitting on the front porch in a rocking chair. At night I could see the stars and fire flies. Breakfast with Denise, the hostess, was also delightful. I will definitely return when in the area hiking. "

A verified traveller stayed at The Destination B&B

Posted 7 days ago

Private Country Getaway 20 minutes from downtown Louisville, KY

5/5 Excellent

Perfect family getaway

"We had a great time at this property. The house is really cool and the different levels makes it fun for a family to have their own space. Everything is very clean and organized. The pool is nice and I didn’t even realize there’s a hot tub which we used a lot. The owner, Dustin, is wonderful and on top of things. This is one of those places that we would definitely come back to! "

A verified traveller from Bloomington stayed at Private Country Getaway 20 minutes from downtown Louisville, KY

Posted 8 days ago

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

5/5 Excellent

"Thank you for a wonderful week in Henryville! We absolutely loved your home! With the 4 bedrooms, it slept 5 of us comfortably. It was so clean, and we saw no bugs at all!! The details in your decor throughout the house were loved by all. We enjoyed the hot tub and time together on the outside decks. Thanks so much! We are hoping to be back sometime soon! "

A verified traveller from IN stayed at Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Posted 3 weeks ago

5/5 Excellent

"Excellent communication, fast responses, very accommodating. The layout is fantastic with lots of open space, comfortable bedrooms, and excellent amenities. The backyard is absolutely huge, probably 3 acres or so. Would stay again for sure."

A verified traveller stayed at Emerald Lake Retreat Charlestown

Posted 3 weeks ago

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?

5 BR, 4 baths, Pool, HotTub, Family Friendly, near Louisville KY, Private: This holiday home rental outside of South Boston is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.

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Holiday Rentals in South Boston

Check prices for these dates

Holiday Rentals in South Boston

Cozy Country Cabin quiet country retreat

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

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

Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

Emerald Lake Retreat Charlestown

Private Country Getaway 20 minutes from downtown Louisville, KY

All About Alden in Sellersburg, IN

Relaxing Country Getaway

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

Mountain views 15 miles from Louisville. Sleeps 20

Moonlit Cottage Near Louisville

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

Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

Country home with beautiful views and access to hiking, biking, and horse trails

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

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

Pet-friendly Emerald Lake Retreat in Charlestown!

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

Peaceful 2-bedroom cottage in the beautiful Floyds Knobs with Hot Tub & Gym

Stonecrest 620, 2Bd Apt I Free Parking I Pool

Find out more about South Boston

Recent reviews of South Boston properties

Holiday Inn Express & Suites Scottsburg by IHG

Knights Inn and Suites Salem

Hampton Inn & Suites Scottsburg

The Destination B&B

Ramada by Wyndham Sellersburg/Louisville North

Private Country Getaway 20 minutes from downtown Louisville, KY

Campbell's Motel

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Emerald Lake Retreat Charlestown

Frequently asked questions