A forest path with a metal archway supported by concrete pillars.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Charlestown vacation homes

A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

1. Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (25 reviews)
"Amazing, would stay again in a heartbeat"
United States
Ian M.
The price is ￥17,679
￥26,220 total
includes taxes & fees
Oct 20 - Oct 21
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Room

2. Country living minutes away from Churchill Downs, Airport, major attractions.

Country living minutes away from Churchill Downs, Airport, major attractions.
Charlestown
9.6 out of 10, Exceptional, (7 reviews)
"So glad we went here for our mini getaway! Definitely a unique place to stay. Room was great and we got to tour other areas in and around the castle. David is a great host and we enjoyed talking with him! Going to try and make it back up for the festival this fall."
United States
Cari H.
The price is ￥19,739
￥30,335 total
includes taxes & fees
Oct 28 - Oct 29
Country living minutes away from Churchill Downs, Airport, major attractions.
A spacious living room with a large sofa, a coffee table, and a TV. There is a balcony with a view of a lake.

3. 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"
United States
Thomas c.
The price is ￥43,773
￥94,909 total
includes taxes & fees
Oct 7 - Oct 8
The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!
A wooden swing bed with a pergola roof, string lights, and a wooden deck.

4. 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 Louisville
Jeffersonville
9.6 out of 10, Exceptional, (17 reviews)
"The property was very nice for our family getaway, would book again."
United States
Roberta
The price is ￥26,883
￥59,719 total
includes taxes & fees
Oct 26 - Oct 27
King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville
A living room with a sectional sofa, a fireplace, a flat-screen TV, and a zebra-patterned chair.

5. 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 Row
Clarksville
9.0 out of 10, Wonderful, (11 reviews)
"Was a great time and very clean "
United States
Jeff B.
The price is ￥11,370
￥32,655 total
includes taxes & fees
Oct 8 - Oct 9
Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum Row
A living room with a glass coffee table, two armchairs, a sofa, a TV, and a bookshelf.

6. 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, (52 reviews)
"Nice property, we would stay again"
United States
Allan A.
The price is ￥11,839
￥33,534 total
includes taxes & fees
Nov 1 - Nov 2
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
A living room with a sofa, armchair, coffee table, and a dining area with a table and chairs.

7. The Whiskey Stop! A Spacious Highlands Retreat

The Whiskey Stop! A Spacious Highlands Retreat
Germantown
10.0 out of 10, Exceptional, (79 reviews)
"It was perfect for our stay very comfortable and we enjoyed it very much"
United States
Lester W.
The price is ￥10,738
￥29,777 total
includes taxes & fees
Oct 26 - Oct 27
The Whiskey Stop! A Spacious Highlands Retreat
A patio with a table and chairs, surrounded by a wooden fence and tall, conical trees.

8. Bourbon Belle- Cozy Germantown home with parking!

Bourbon Belle- Cozy Germantown home with parking!
Germantown
10.0 out of 10, Exceptional, (79 reviews)
"We've stayed here a few times in the past and it's always been a great experience!"
United States
Paul H.
The price is ￥6,822
￥25,253 total
includes taxes & fees
Oct 7 - Oct 8
Bourbon Belle- Cozy Germantown home with parking!
A backyard with a barbecue grill, outdoor seating, and a fire pit.

9. Stable #3 ~ Mini Golf, Foosball, BBQ, Fire Pits

Stable #3 ~ Mini Golf, Foosball, BBQ, Fire Pits
Irish Hill
10.0 out of 10, Exceptional, (11 reviews)
"Very nice place, great location for us."
United States
peter m.
The price is ￥8,792
￥35,163 total
includes taxes & fees
Oct 7 - Oct 8
Stable #3 ~ Mini Golf, Foosball, BBQ, Fire Pits
A modern kitchen with a central island, bar stools, pendant lights, and a large window with curtains.

10. The Shotgun Rye! Your Bourbon home near Downtown

The Shotgun Rye! Your Bourbon home near Downtown
Germantown
10.0 out of 10, Exceptional, (78 reviews)
"Great location within driving distance to all the tourist destinations. Easy parking and all the amenities you would need! Would def stay again!"
United States
Jered J.
The price is ￥8,587
￥30,021 total
includes taxes & fees
Oct 7 - Oct 8
The Shotgun Rye! Your Bourbon home near Downtown
A modern living room with a sofa, coffee table, TV, and wooden cabinet.

11. Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard

Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
Jeffersonville
10.0 out of 10, Exceptional, (11 reviews)
"Has all the amenities you would need and is in a quiet neighborhood. Great for families."
United States
Stephen
The price is ￥18,949
￥40,327 total
includes taxes & fees
Oct 25 - Oct 26
Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
A modern kitchen with granite countertops, stainless steel appliances, and pendant lighting.

12. 3-bedroom bungalow with , WiFi in Jeffersonville

3-bedroom bungalow with , WiFi in Jeffersonville
Jeffersonville
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."
United States
Aimee H.
3-bedroom bungalow with , WiFi in Jeffersonville
A kitchen with wooden cabinets, a stove, a microwave, a sink, and a refrigerator.

13. St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (14 reviews)
"cute housegreat location easy peasy"
United States
Lisa M.
The price is ￥12,080
￥52,328 total
includes taxes & fees
Oct 12 - Oct 13
St. Matthew’s - Walk to Shops & Restaurants
A covered patio with a door, two wicker chairs, and string lights.

14. Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (8 reviews)
"Great location nice place comfortable "
United States
Hipolito C.
Cozy Tiny House in Scottsburg
A living room with a grey sofa, blue ottoman, and a ceiling fan.

15. Walk to EVERYTHING- Top Restaurants/Shopping/Nightlife - Bardstown Rd /Highlands

Walk to EVERYTHING- Top Restaurants/Shopping/Nightlife - Bardstown Rd /Highlands
Louisville
10.0 out of 10, Exceptional, (4 reviews)
"Great little spot, and communication with the host was phenomenal!"
United States
Kate J.
Walk to EVERYTHING- Top Restaurants/Shopping/Nightlife - Bardstown Rd /Highlands
A covered outdoor seating area with Adirondack chairs and a fire pit, surrounded by trees and gravel.

16. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
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 "
United States
MaKayla Q.
The price is ￥9,313
￥30,823 total
includes taxes & fees
Oct 12 - Oct 13
Modern cabin very close to scenic riverfront walks
A covered porch with a wooden bench, a welcome mat, and potted plants.

17. ✪Heated Pool, Firepit, Bikes, Grill, Pets✪

✪Heated Pool, Firepit, Bikes, Grill, Pets✪
Jeffersonville
8.0 out of 10, Very good, (32 reviews)
"Cute house with all the comforts needed for a fun family stay."
United States
Anonymous traveler
The price is ￥16,849
￥50,977 total
includes taxes & fees
Oct 7 - Oct 8
✪Heated Pool, Firepit, Bikes, Grill, Pets✪
Living area

18. Highlands Escape: King Bed, Coffee Bar, BBQ & WiFi

Highlands Escape: King Bed, Coffee Bar, BBQ & WiFi
Phoenix Hill
9.4 out of 10, Exceptional, (40 reviews)
"Solid place, close to everything, perfect for Bourbon Trail trip!"
United States
Jake F.
The price is ￥9,155
￥28,496 total
includes taxes & fees
Oct 12 - Oct 13
Highlands Escape: King Bed, Coffee Bar, BBQ & WiFi
A bedroom with a bed, nightstands, a ceiling fan, and a window with shutters.

19. Convenient & Cozy! Close to everything Louisville!

Convenient & Cozy! Close to everything Louisville!
Belknap
The price is ￥19,959
￥42,947 total
includes taxes & fees
Oct 7 - Oct 8
Convenient & Cozy! Close to everything Louisville!
Private kitchen

20. Uptown Class

Uptown Class
New Albany
9.8 out of 10, Exceptional, (37 reviews)
"Communication was good,very responsive"
United States
Jerrel
The price is ￥23,687
￥71,376 total
includes taxes & fees
Oct 14 - Oct 15
Uptown Class
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 Charlestown Hotel Reviews

The Brown Hotel

The Brown Hotel

10/10 Excellent
"I will come back again"
Chris 1-night trip
Posted 2 hours ago
The Brown Hotel

Find out more about Charlestown

Charlestown Vacation Homes information

Number of reviews
486
Accommodation
795 Vacation Homes
Lowest Price
￥25,253
Highest Price
￥94,909