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

Holiday Homes in Charlestown

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Charlestown holiday 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, (27 reviews)
"The carriage house was very roomy and nice. We would definitely stay here again."
United States
Pam
The price is AU$238
includes taxes & fees
23 Nov - 24 Nov
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A spacious living room with a large sofa, a coffee table, and a TV. There is a balcony with a view of a lake.

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"
United States
Thomas c.
The price is AU$921
includes taxes & fees
28 Oct - 29 Oct
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.

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 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 AU$508
includes taxes & fees
25 Oct - 26 Oct
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.

4. 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, (13 reviews)
"Was a great time and very clean "
United States
Jeff B.
The price is AU$272
includes taxes & fees
27 Oct - 28 Oct
Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum Row
A backyard with a barbecue grill, outdoor seating, and a fire pit.

5. 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 AU$282
includes taxes & fees
26 Oct - 27 Oct
Stable #3 ~ Mini Golf, Foosball, BBQ, Fire Pits
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 AU$306
includes taxes & fees
1 Nov - 2 Nov
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
A dining area with a wooden table, chairs, and a vase of flowers.

7. Historic Riverview Stay | 1 Mi Downtown Louisville

Historic Riverview Stay | 1 Mi Downtown Louisville
Jeffersonville
10.0 out of 10, Exceptional, (1 review)
"It was a great place to stay! "
United States
Lexi S.
The price is AU$342
includes taxes & fees
25 Oct - 26 Oct
Historic Riverview Stay | 1 Mi Downtown Louisville
A modern kitchen with granite countertops, stainless steel appliances, and pendant lighting.

8. 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.
The price is AU$605
includes taxes & fees
24 Oct - 25 Oct
3-bedroom bungalow with , WiFi in Jeffersonville
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

9. 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 AU$283
includes taxes & fees
5 Nov - 6 Nov
Modern cabin very close to scenic riverfront walks
A bedroom with a bed, nightstands, a ceiling fan, and a window with shutters.

10. Convenient & Cozy! Close to everything Louisville!

Convenient & Cozy! Close to everything Louisville!
Belknap
The price is AU$389
includes taxes & fees
23 Nov - 24 Nov
Convenient & Cozy! Close to everything Louisville!
A fire feature with glasses of beverages, a wooden bench, and a covered outdoor seating area.

11. LUX Waterside Retreat with Geo Dome + Outdoor Fire Table, Historic Property

LUX Waterside Retreat with Geo Dome + Outdoor Fire Table, Historic Property
Prospect
10.0 out of 10, Exceptional, (13 reviews)
"Absolutely love this property. We will stay everytime we come to Louisville. Can’t say enough about how great the home, area and host were"
United States
Lisa R.
The price is AU$654
includes taxes & fees
25 Oct - 26 Oct
LUX Waterside Retreat with Geo Dome + Outdoor Fire Table, Historic Property
A backyard with a barbecue grill, outdoor seating, and a fire pit.

12. Stable #5 ~ Mini Golf, Fire Pits, Games, Walkable

Stable #5 ~ Mini Golf, Fire Pits, Games, Walkable
Irish Hill
10.0 out of 10, Exceptional, (6 reviews)
"The location is right down the street from many shops and restaurants. Downtown Louisville is 10 minutes and an easy drive. All amenities were great and plenty of room in the kitchen.Host was amazing and the property was very clean."
United States
Eric K.
The price is AU$374
includes taxes & fees
27 Oct - 28 Oct
Stable #5 ~ Mini Golf, Fire Pits, Games, Walkable
A two-story residential building with a front porch, a wooden door, and a number '414' on the right side.

13. The Curated Chateau—Minutes from Louisville

The Curated Chateau—Minutes from Louisville
New Albany
9.8 out of 10, Exceptional, (47 reviews)
"It was a perfect stay for our weekend at Churchill Downs."
United States
Peggy S.
The price is AU$403
includes taxes & fees
25 Oct - 26 Oct
The Curated Chateau—Minutes from Louisville
A modern kitchen with dark cabinetry, a central island, and pendant lighting.

14. Putt Putt House by Louisville Walking Bridge

Putt Putt House by Louisville Walking Bridge
Jeffersonville
10.0 out of 10, Exceptional, (17 reviews)
"The house and location were fantastic! The house had everything we needed and was very thoughtfully supplied."
United States
Emily F.
The price is AU$417
includes taxes & fees
9 Nov - 10 Nov
Putt Putt House by Louisville Walking Bridge
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.
The price is AU$298
includes taxes & fees
25 Oct - 26 Oct
Walk to EVERYTHING- Top Restaurants/Shopping/Nightlife - Bardstown Rd /Highlands
A patio with Adirondack chairs, a fire pit, and a small shed in a garden setting.

16. Spacious Highlands gem near Bellarmine & Bardstown

Spacious Highlands gem near Bellarmine & Bardstown
Belknap
10.0 out of 10, Exceptional, (4 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."
United States
Laura C.
The price is AU$470
includes taxes & fees
25 Oct - 26 Oct
Spacious Highlands gem near Bellarmine & Bardstown
A bedroom with a bed, a hanging coat rack, a bathroom with a shower, and a kitchen area.

17. The Booker Noe Suite | Brick Home w/ Modern Design

The Booker Noe Suite | Brick Home w/ Modern Design
Taylor Berry
The price is AU$256
includes taxes & fees
1 Nov - 2 Nov
The Booker Noe Suite | Brick Home w/ Modern Design
A white sign with the words 'oh hello' in a cursive font, placed on a white surface with a plant and a lantern in the background.

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)
"The house was super cute inside, the floors were a bit dirty. Only issue we had was the crackhead fight right outside where they were hurling jugs of water and bags of mulch at each other in the middle of the street and the poor old man next door trying to break it up. Good place for a quick stay."
United States
Shauna H.
The price is AU$292
includes taxes & fees
25 Oct - 26 Oct
Highlands Escape: King Bed, Coffee Bar, BBQ & WiFi
A modern kitchen with white cabinets, a large island with bar stools, a built-in oven, and a stainless steel refrigerator.

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

Country home with beautiful views and access to hiking, biking, and horse trails
Henryville
9.8 out of 10, Exceptional, (44 reviews)
"Loved the dog-friendly house that even had a nice small fenced in area. Super quiet and close to the Knobstone trail for some exploring. The house was easy to find and access and the host was friendly. Thanks for the great place to stay!"
United States
Forrest K.
The price is AU$406
includes taxes & fees
26 Oct - 27 Oct
Country home with beautiful views and access to hiking, biking, and horse trails
A two-story house with a front porch, a chimney, and a number '3935' on the door.

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

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (15 reviews)
"cute housegreat location easy peasy"
United States
Lisa M.
The price is AU$487
includes taxes & fees
1 Nov - 2 Nov
St. Matthew’s - Walk to Shops & Restaurants
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

Hyatt Regency Louisville

Hyatt Regency Louisville

10/10 Excellent
"Great hotel"
Leo 1-night trip
Posted less than an hour ago
Hyatt Regency Louisville

Find out more about Charlestown

Charlestown Holiday Homes information

Number of reviews
324
Accommodation
802 Holiday Homes
Lowest Price
AU$238
Highest Price
AU$921