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

Charlestown Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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, (27 reviews)
"The carriage house was very roomy and nice. We would definitely stay here again."
United States
Pam
The price is CA $148
CA $223 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $455
CA $926 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $215
CA $511 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $78
CA $264 total
includes taxes & fees
Oct 28 - Oct 29
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 CA $48
CA $275 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $105
CA $298 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $99
CA $331 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $308
CA $608 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $60
CA $246 total
includes taxes & fees
Oct 26 - Oct 27
Modern cabin very close to scenic riverfront walks
A two-story brick house with a front porch, a staircase, and a well-maintained garden.

10. Convenient & Cozy! Close to everything Louisville!

Convenient & Cozy! Close to everything Louisville!
Belknap
The price is CA $182
CA $395 total
includes taxes & fees
Nov 19 - Nov 20
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 CA $290
CA $656 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $64
CA $363 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $175
CA $400 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $140
CA $411 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $103
CA $293 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $132
CA $478 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $76
CA $248 total
includes taxes & fees
Nov 3 - Nov 4
The Booker Noe Suite | Brick Home w/ Modern Design
A bed with a pillow that reads 'Sweet dreams' and a neon sign on the wall.

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 CA $105
CA $287 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $231
CA $400 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $125
CA $489 total
includes taxes & fees
Nov 1 - Nov 2
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Charlestown Hotel Reviews

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

10/10 Excellent
"Decent place to stay, close to campus"
Lisel 2-night trip
Posted 1 hour ago
Crowne Plaza Louisville Airport Expo Ctr by IHG

Find out more about Charlestown

Charlestown Vacation Homes information

Number of reviews
324
Accommodation
802 Vacation Homes
Lowest Price
CA $223
Highest Price
CA $926

Explore a world of travel with Expedia