South Boston Holiday Rentals

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Holiday Rentals in South Boston

Cozy Country Cabin quiet country retreat

10.0 out of 10, Exceptional, (179)
"We very much enjoyed our stay at this cabin. "
The price is NZ$356
includes taxes & fees
29 Sept - 30 Sept
Cozy Country Cabin quiet country retreat

Relaxing Country Getaway

9.4 out of 10, Exceptional, (39)
"It was a very nice little get away without going too far. Everything was clean, including the hot tub. We will definitely keep this place in mind in the future!"
Relaxing Country Getaway

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

10.0 out of 10, Exceptional, (9)
"Was the perfect little overnight stay! "
The price is NZ$274
includes taxes & fees
26 Oct - 27 Oct
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

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

9.8 out of 10, Exceptional, (18)
"Excellent place very nice "
35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.

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

10.0 out of 10, Exceptional, (149)
"Had a group of friends stay for a weekend trip, property is well maintained and has fantastic amenities. "
The price is NZ$728
includes taxes & fees
29 Sept - 30 Sept
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Mountain views 15 miles from Louisville. Sleeps 20

10.0 out of 10, Exceptional, (6)
"Great location and stunning views!!"
Mountain views 15 miles from Louisville. Sleeps 20

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

2.0 star property
10.0 out of 10, Exceptional, (12)
"Excellent place to stay. Everything was absolutely amazing. "
The price is NZ$513
includes taxes & fees
29 Sept - 30 Sept
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!

10.0 out of 10, Exceptional, (7)
"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!"
Anjuna River House - the hidden Scandi cabin on 12 acres in Southern Indiana!

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

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

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

10.0 out of 10, Exceptional, (25)
"Can’t say enough good things about this place!"
The price is NZ$440
includes taxes & fees
30 Sept - 1 Oct
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

10.0 out of 10, Exceptional, (118)
"We enjoyed our stay at the home and the use of the pool and great back yard."
5 BR, 4 baths, Pool, HotTub, Family Friendly, near Louisville KY, Private

Moonlit Cottage Near Louisville

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...
The price is NZ$413
includes taxes & fees
30 Sept - 1 Oct
Moonlit Cottage Near Louisville

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

10.0 out of 10, Exceptional, (37)
"We love staying here for our annual Kayak trip!"
The price is NZ$1,106
includes taxes & fees
27 Oct - 28 Oct
Tell your family to meet you here!<br>No Drinking Parties

Emerald Lake Retreat Charlestown

10.0 out of 10, Exceptional, (2)
"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!"
The price is NZ$724
includes taxes & fees
29 Sept - 30 Sept
Emerald Lake Retreat Charlestown

Stonecrest 620, 2Bd Apt I Free Parking I Pool

9.0 out of 10, Wonderful, (2)
"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...
Stonecrest 620, 2Bd Apt I Free Parking I Pool

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

4.0 star property
9.4 out of 10, Exceptional, (10)
"Very nice house in a nice neighborhood, spacious home environmental, felt more that at home there,"
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

Stonecrest 623, 2Bd Apt I Free Parking I Pool

2.0 star property
Stonecrest 623, 2Bd Apt I Free Parking I Pool

Stonecrest 722, Modern 2Bd Apt I Parking I Gym

Stonecrest 722, Modern 2Bd Apt I Parking I Gym

Stonecrest 910, 2Bd Apt I Free Parking I Pool

Stonecrest 910, 2Bd Apt I Free Parking I Pool

Stonecrest 822, 2Bd Apt I Free Parking I Pool

Stonecrest 822, 2Bd Apt I Free Parking I Pool
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

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$274 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?

Relaxing Country Getaway: This holiday home rental outside of South Boston is located in a rural location, and has 1 hot tub, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware.

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.