Holiday Rentals in South Boston

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Holiday Rentals in South Boston

Relaxing Country Getaway

9.4 out of 10, Exceptional, (35)
"Wonderful stay, very private. Cozy place perfect for couples looking to unwind. Would stay again."
Relaxing Country Getaway

Cozy Country Cabin quiet country retreat

10.0 out of 10, Exceptional, (177)
"We very much enjoyed our stay at this cabin. "
The price is €181
includes taxes & fees
18 Aug - 19 Aug
Cozy Country Cabin quiet country retreat

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

10.0 out of 10, Exceptional, (149)
"A beautiful place and just what we were looking for to get a bunch of people together for our DnD game. Host was responsive an accommodating to ensure our stay was enjoyable. Would stay again! "
The price is €338
includes taxes & fees
18 Aug - 19 Aug
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Private Country Getaway 20 minutes from downtown Louisville, KY

9.8 out of 10, Exceptional, (36)
"Beautiful, quiet location with great outdoor spaces to enjoy, reasonable kitchen equipment, lovely pool and spa. Dustin was very helpful and accommodating. Place was easy to find. We enjoyed our stay very much!"
Private Country Getaway 20 minutes from downtown Louisville, KY

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

10.0 out of 10, Exceptional, (7)
"Was the perfect little overnight stay! "
The price is €139
includes taxes & fees
18 Aug - 19 Aug
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

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

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."
Emerald Lake Retreat Charlestown

All About Alden in Sellersburg, IN

9.6 out of 10, Exceptional, (4)
"Our host was great she was always available for us from the start until we left. Responding to any questions we had and the welcome book was loaded with suggestions on what we could do during our stay.Thanks"
The price is €268
includes taxes & fees
1 Sept - 2 Sept
All About Alden in Sellersburg, IN

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 €233
includes taxes & fees
2 Sept - 3 Sept
Country home with beautiful views and access to hiking, biking, and horse trails

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.

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

10.0 out of 10, Exceptional, (116)
"Awesome home and the20 of us enjoyed it all despite the rainy weather. Very remote but outstanding property! "
5 BR, 4 baths, Pool, HotTub, Family Friendly, near Louisville KY, Private

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

10.0 out of 10, Exceptional, (36)
"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 €526
includes taxes & fees
18 Aug - 19 Aug
Tell your family to meet you here!<br>No Drinking Parties

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!

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

2.0 star property
10.0 out of 10, Exceptional, (10)
"No if’s or but’s, a very nice house with the added benefit of being right next to a State Recreation area with hiking, fishing and swimming. Strongly recommended."
The price is €281
includes taxes & fees
15 Sept - 16 Sept
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

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.

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

Pet-friendly Emerald Lake Retreat in Charlestown!

3.0 star property
Pet-friendly Emerald Lake Retreat in 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 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

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.