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Our top choices for Charlestown holiday homes
1. Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, ACCharlestown
10.0 out of 10, Exceptional, (30 reviews)
"The carriage house was very roomy and nice. We would definitely stay here again."
Pam
The price is HK$824
HK$1,126 total
includes taxes & fees
16 Nov - 17 Nov
2. The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!
The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!Prospect
9.8 out of 10, Exceptional, (10 reviews)
"My family and I had a wonderful trip. The house was absolutely beautiful. Everything was clean and well taken care of we couldn’t have asked for a better vacation"
Thomas c.
The price is HK$2,746
HK$5,138 total
includes taxes & fees
1 Dec - 2 Dec
3. King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville
King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T LouisvilleJeffersonville
9.6 out of 10, Exceptional, (17 reviews)
"The property was very nice for our family getaway, would book again."
Roberta
The price is HK$1,202
HK$2,745 total
includes taxes & fees
16 Nov - 17 Nov
4. Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.New Albany
10.0 out of 10, Exceptional, (53 reviews)
"Nice property, we would stay again"
Allan A.
The price is HK$588
HK$1,596 total
includes taxes & fees
16 Nov - 17 Nov
5. The Booker Noe Suite | Brick Home w/ Modern Design
The Booker Noe Suite | Brick Home w/ Modern DesignTaylor Berry
The price is HK$364
HK$1,622 total
includes taxes & fees
19 Nov - 20 Nov
6. New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!South Louisville
9.8 out of 10, Exceptional, (53 reviews)
"Great stay and great host"
Chayil B.
The price is HK$353
HK$1,339 total
includes taxes & fees
18 Nov - 19 Nov
7. Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum Row
Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum RowClarksville
9.0 out of 10, Wonderful, (13 reviews)
"Was a great time and very clean "
Jeff B.
The price is HK$612
HK$1,454 total
includes taxes & fees
7 Dec - 8 Dec
8. Stable #3 ~ Mini Golf, Foosball, BBQ, Fire Pits
Stable #3 ~ Mini Golf, Foosball, BBQ, Fire PitsIrish Hill
10.0 out of 10, Exceptional, (11 reviews)
"Very nice place, great location for us."
peter m.
The price is HK$289
HK$1,703 total
includes taxes & fees
17 Nov - 18 Nov
9. Modern cabin very close to scenic riverfront walks
Modern cabin very close to scenic riverfront walksHanover
9.4 out of 10, Exceptional, (20 reviews)
"The space was very clean and had everything we needed! It was so close to everything but in its own secluded spot at the same time. We loved our stay "
MaKayla Q.
The price is HK$364
HK$1,827 total
includes taxes & fees
3 Dec - 4 Dec
10. Cozy NuLu Getaway | Private Yard + Free Parking
Cozy NuLu Getaway | Private Yard + Free ParkingPhoenix Hill
9.2 out of 10, Wonderful, (29 reviews)
"Place was very clean. Close to downtown & dining "
Tracy H.
The price is HK$424
HK$1,431 total
includes taxes & fees
15 Dec - 16 Dec
11. Riverview Retreat Only 1 Mi Downtown Louisville!
Riverview Retreat Only 1 Mi Downtown Louisville!Jeffersonville
The price is HK$596
HK$2,643 total
includes taxes & fees
18 Nov - 19 Nov
12. Convenient & Cozy! Close to everything Louisville!
Convenient & Cozy! Close to everything Louisville!Belknap
The price is HK$1,019
HK$2,066 total
includes taxes & fees
16 Nov - 17 Nov
13. Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with YardJeffersonville
10.0 out of 10, Exceptional, (13 reviews)
"Has all the amenities you would need and is in a quiet neighborhood. Great for families."
Stephen
14. 3-bedroom bungalow with , WiFi in Jeffersonville
3-bedroom bungalow with , WiFi in JeffersonvilleJeffersonville
10.0 out of 10, Exceptional, (3 reviews)
"It was a short 15 minute drive from the University of Louisville. So would be a perfect fit for anyone coming into town for a sporting event at UofL. We rented it for Kentucky Derby Weekend and it was just what we needed!!! Close enough to the track but outside the general “chaos” that surrounds The Derby."
Aimee H.
The price is HK$1,726
HK$3,271 total
includes taxes & fees
28 Nov - 29 Nov
15. The Matt Winn Suite | A cozy & modern brick home!
The Matt Winn Suite | A cozy & modern brick home!Taylor Berry
The price is HK$458
HK$1,953 total
includes taxes & fees
18 Nov - 19 Nov
16. Spacious Highlands gem near Bellarmine & Bardstown
Spacious Highlands gem near Bellarmine & BardstownBelknap
10.0 out of 10, Exceptional, (5 reviews)
"The property was perfect for quick family gathering. John was a great host. He was super responsive and I would glad rent from him again."
Laura C.
The price is HK$797
HK$3,598 total
includes taxes & fees
16 Nov - 17 Nov
17. Spacious home near Downtown w/ backyard & parking!
Spacious home near Downtown w/ backyard & parking!Clifton Heights
9.6 out of 10, Exceptional, (4 reviews)
"Quiet neighborhood, convenient location, spacious yard for our dog."
Cameron B.
The price is HK$659
HK$2,213 total
includes taxes & fees
16 Nov - 17 Nov
18. Dolphins Cove | Hot Tub | Near Churchill Downs 2 Bedroom
Dolphins Cove | Hot Tub | Near Churchill Downs 2 BedroomTaylor Berry
8.4 out of 10, Very good, (7 reviews)
"Loved the backyard "
Jeremy P.
The price is HK$471
HK$1,280 total
includes taxes & fees
19 Nov - 20 Nov
19. Professionally curated home with private backyard
Professionally curated home with private backyardPhoenix Hill
9.4 out of 10, Exceptional, (31 reviews)
"Good stay"
Refugio R.
The price is HK$534
HK$1,929 total
includes taxes & fees
15 Dec - 16 Dec
20. Dragons Perch | Hot Tub | 2 Bedroom
Dragons Perch | Hot Tub | 2 BedroomTaylor Berry
The price is HK$518
HK$1,132 total
includes taxes & fees
19 Nov - 20 Nov
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.
Learn more about Charlestown
Explore the historic Charlestown Square where local festivals showcase the town's community spirit throughout the year. Families flock to Charlestown Family Activities Park for its splash pad, playground, and picnic areas perfect for summer afternoons.
