South Boston Holiday Rentals

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Holiday Rentals in South Boston

Relaxing Country Getaway

9.4 out of 10, Exceptional, (33)
"Wonderful stay, very private. Cozy place perfect for couples looking to unwind. Would stay again."
Relaxing Country Getaway

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

10.0 out of 10, Exceptional, (5)
"Was the perfect little overnight stay! "
The price is NZ$265
includes taxes & fees
7 Aug - 8 Aug
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

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

10.0 out of 10, Exceptional, (146)
"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!"
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

10.0 out of 10, Exceptional, (112)
"Loved this property!!! We would definitely stay again!"
5 BR, 4 baths, Pool, HotTub, Family Friendly, near Louisville KY, Private

Emerald Lake Retreat Charlestown

10.0 out of 10, Exceptional, (1)
"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."
The price is NZ$748
includes taxes & fees
22 July - 23 July
Emerald Lake Retreat Charlestown

Private Country Getaway 20 minutes from downtown Louisville, KY

10.0 out of 10, Exceptional, (35)
"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!"
Private Country Getaway 20 minutes from downtown Louisville, KY

Cozy Country Cabin quiet country retreat

10.0 out of 10, Exceptional, (176)
"We very much enjoyed our stay at this cabin. "
The price is NZ$346
includes taxes & fees
24 July - 25 July
Cozy Country Cabin quiet country retreat

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

All About Alden in Sellersburg, IN

9.4 out of 10, Exceptional, (3)
"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!"
The price is NZ$408
includes taxes & fees
20 Aug - 21 Aug
All About Alden in Sellersburg, IN

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...
Moonlit Cottage Near Louisville

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

10.0 out of 10, Exceptional, (35)
"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!"
The price is NZ$1,007
includes taxes & fees
30 July - 31 July
Tell your family to meet you here!<br>No Drinking Parties

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

2.0 star property
10.0 out of 10, Exceptional, (10)
"Wonderful Host and property."
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

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, (23)
"Can’t say enough good things about this place!"
The price is NZ$420
includes taxes & fees
23 July - 24 July
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!

10.0 out of 10, Exceptional, (6)
"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."
Anjuna River House - the hidden Scandi cabin on 12 acres in Southern Indiana!

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

10.0 out of 10, Exceptional, (16)
"Excellent place very nice "
35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.

Pet-friendly Emerald Lake Retreat in Charlestown!

3.0 star property
Pet-friendly Emerald Lake Retreat in Charlestown!

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 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

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

The price is NZ$963
includes taxes & fees
31 July - 1 Aug
Peaceful 2-bedroom cottage in the beautiful Floyds Knobs with Hot Tub & 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

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 a coffee maker.

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.