South Boston Holiday Rentals

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Holiday Rentals in South Boston

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

Henryville
10.0 out of 10, Exceptional, (153)
"Peaceful, beautiful place. Very homey and excellent outdoor firepit. Did not like the downstairs shower. All other aspects were great and the artistic detail was excellent."
United States
Mary Nugent T.
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Cozy Tiny House in Scottsburg

Scottsburg
9.0 out of 10, Wonderful, (2)
"Host was nice. The tiny house was cute and very clean. I wish there had been a blanket for the sofa bed and a toaster. But there was a Dollar General just down the street. All in all is was a sweet little place to stay."
United States
Thomas C.
The price is NZ$311
includes taxes & fees
9 Dec - 10 Dec
Cozy Tiny House in Scottsburg

Cozy Country Cabin quiet country retreat

Orleans
10.0 out of 10, Exceptional, (183)
"We very much enjoyed our stay at this cabin. "
United States
Ashley Y.
The price is NZ$339
includes taxes & fees
14 Nov - 15 Nov
Cozy Country Cabin quiet country retreat

Large Group Rental Near Louisville with Mountain Views

Wood Township
10.0 out of 10, Exceptional, (6)
"Great property with plenty of room and activities!"
United States
Laura A.
Large Group Rental Near Louisville with Mountain Views

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

Memphis
10.0 out of 10, Exceptional, (11)
"Was the perfect little overnight stay! "
United States
Billie Jo M.
The price is NZ$280
includes taxes & fees
24 Nov - 25 Nov
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

Relaxing Country Getaway

Lexington
9.4 out of 10, Exceptional, (42)
"This place is a definite need to stay vacation spot!!! The attention to detail inside and outside this home is spectacular!!!"
United States
mark b.
Relaxing Country Getaway

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 NZ$535
includes taxes & fees
16 Nov - 17 Nov
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

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

New Pekin
10.0 out of 10, Exceptional, (7)
"Our family was in the area to hike the Knobstone Trail and Anjuna house was a perfect resting spot when we were done for the day. The home was clean and well equipped, the views fantastic and the teenagers loved the hammock. We thoroughly enjoyed our stay and hope to return again in the future!"
United States
Veronica S.
Anjuna River House - the hidden Scandi cabin on 12 acres in Southern Indiana!

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

Emerald Lake Retreat Charlestown

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

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

Henryville
10.0 out of 10, Exceptional, (25)
"We had an amazing time at this Vrbo rental! The property was exactly as described—clean, well-stocked, and incredibly comfortable. The location was perfect, the host was responsive, helpful, and made the check-in process seamless. We especially loved the views. It truly felt like a home away from home. We would absolutely stay here again and recommend it to anyone looking for a great place to stay!"
United States
Amy H.
The price is NZ$445
includes taxes & fees
17 Nov - 18 Nov
Country home with beautiful views and access to hiking, biking, and horse trails

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

Fredericksburg
10.0 out of 10, Exceptional, (118)
"2nd stay here. Accommodations great. Space, pool and hot tub all wonderful. The gas grill is on its last legs and unfortunately we had planned dinners around it so we had to use the oven. "
United States
Debra B.
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.

New Albany
9.4 out of 10, Exceptional, (10)
"Everything was great. Great communication and check in."
United States
af w.
2600 SF home 15 Minutes from Downtown Louisville in New Albany. Full basement.

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

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

Fredericksburg
9.8 out of 10, Exceptional, (19)
"Excellent place very nice "
United States
Donna G.
35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.

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.
The price is NZ$482
includes taxes & fees
17 Nov - 18 Nov
Moonlit Cottage Near Louisville

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

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

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

Hardinsburg
10.0 out of 10, Exceptional, (37)
"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!"
United States
Leanne G.
The price is NZ$1,062
includes taxes & fees
16 Nov - 17 Nov
Tell your family to meet you here!<br>No Drinking Parties

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 NZ$555
includes taxes & fees
18 Nov - 19 Nov
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

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 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, 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 NZ$280 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. 

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?

Cozy Tiny House in Scottsburg: This holiday home rental outside of 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 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.