Holiday Homes in Charlestown

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Charlestown holiday homes

Fridge, microwave, oven, stovetop

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, (14 reviews)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
The price is NZ$243
includes taxes & fees
21 Feb - 22 Feb
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Property grounds

Cozy 3BR Derby Favorite Unit Near Churchill Downs!

Cozy 3BR Derby Favorite Unit Near Churchill Downs!
Merriwether
10.0 out of 10, Exceptional, (3 reviews)
"Place was clean and fit our needs well. "
United States
sean g.
The price is NZ$332
includes taxes & fees
17 Feb - 18 Feb
Cozy 3BR Derby Favorite Unit Near Churchill Downs!
Fridge, microwave, oven, stovetop

Modern Nature Cabin | Private Escape in the Forest

Modern Nature Cabin | Private Escape in the Forest
Hanover
9.8 out of 10, Exceptional, (8 reviews)
"Very nice facility and relaxing setting . "
United States
Robert V.
The price is NZ$309
includes taxes & fees
12 Mar - 13 Mar
Modern Nature Cabin | Private Escape in the Forest
Interior

The Pegasus Luxury and Location!

The Pegasus Luxury and Location!
Bonnycastle
10.0 out of 10, Exceptional, (10 reviews)
"House was in great location and is very well maintained. We would recommend the rental to anyone wanting great accommodations."
United States
Shannon L.
The Pegasus Luxury and Location!
Terrace/patio

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Pendleton
9.8 out of 10, Exceptional, (63 reviews)
"The Tack House was just what we needed for a weekend away while the kids were out camping with the scouts. "
United States
Matt and Nykki B.
The price is NZ$376
includes taxes & fees
3 Mar - 4 Mar
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Interior

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
10.0 out of 10, Exceptional, (23 reviews)
"Very clean place, easy check in, Felix was very nice and super responsive "
United States
Will J.
The price is NZ$302
includes taxes & fees
16 Feb - 17 Feb
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
Fridge, microwave, oven, stovetop

Germantown Fav! BOOK for MATS, DERBY 2026!

Germantown Fav! BOOK for MATS, DERBY 2026!
Germantown
10.0 out of 10, Exceptional, (72 reviews)
"Cute comfortable house would go again"
United States
Hope N.
Germantown Fav! BOOK for MATS, DERBY 2026!
Exterior

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!
Shelby Park
9.6 out of 10, Exceptional, (21 reviews)
"Cute place ! Great area not far from campus and other restaurants ! Great communication from host !"
United States
Lynda M.
The price is NZ$356
includes taxes & fees
19 Feb - 20 Feb
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!
Fridge, microwave, oven, stovetop

Charming house in one of Louisville's most coveted neighborhoods

Charming house in one of Louisville's most coveted neighborhoods
Louisville
10.0 out of 10, Exceptional, (78 reviews)
"Great location, very clean!!!!"
United States
Matt W.
The price is NZ$473
includes taxes & fees
23 Feb - 24 Feb
Charming house in one of Louisville's most coveted neighborhoods
Exterior detail

The Chestnut - Nulu

The Chestnut - Nulu
Phoenix Hill
9.8 out of 10, Exceptional, (34 reviews)
"Great property, pristine and clean and conveniently located with good parking."
United States
David D.
The price is NZ$353
includes taxes & fees
23 Feb - 24 Feb
The Chestnut - Nulu
Exterior detail

The Sweet Retreat Wheelchair Accessible Historic Home

The Sweet Retreat Wheelchair Accessible Historic Home
La Grange
10.0 out of 10, Exceptional, (5 reviews)
"We had a family gathering over Thanksgiving and the large table was very nice and appreciated. Host was very prompt with communication and most everything we needed was there. Would stay again!"
United States
Shelley S.
The price is NZ$620
includes taxes & fees
15 Feb - 16 Feb
The Sweet Retreat Wheelchair Accessible Historic Home
Dining

Stylish Chic Modern, Remodel, Private Yard Deck, Bourbon Trail, Airport, YumYum!

Stylish Chic Modern, Remodel, Private Yard Deck, Bourbon Trail, Airport, YumYum!
Germantown
10.0 out of 10, Exceptional, (4 reviews)
"We loved the kitchen and the bathroom. "
United States
Kat D.
Stylish Chic Modern, Remodel, Private Yard Deck, Bourbon Trail, Airport, YumYum!
Interior

Stylish Jeffersonville Home - Mins from Louisville

Stylish Jeffersonville Home - Mins from Louisville
Jeffersonville
9.2 out of 10, Wonderful, (22 reviews)
"This was a great place for us to stay for an event at the expedition center. Close to the highway for quick access to the city. "
United States
Chad L.
The price is NZ$531
includes taxes & fees
4 Mar - 5 Mar
Stylish Jeffersonville Home - Mins from Louisville
Living area

Stylish House Walking Distance from the Fun of the Highlands!

Stylish House Walking Distance from the Fun of the Highlands!
Phoenix Hill
9.6 out of 10, Exceptional, (24 reviews)
"We will stay here over and over again. It’s a lovely place that a perfect location."
United States
Jennifer H.
The price is NZ$280
includes taxes & fees
16 Feb - 17 Feb
Stylish House Walking Distance from the Fun of the Highlands!
Smart TV, books

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, (5 reviews)
"Super nice place to stay! It is very clean, has all the necessary amenities, and is close to the fun nearby! Host is very communicative and polite. Would definitely recommend staying here!"
United States
Collin R.
The price is NZ$380
includes taxes & fees
23 Feb - 24 Feb
Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
Interior

NEW Cozy Home in Shelby Park | Near Cafes & Stores

NEW Cozy Home in Shelby Park | Near Cafes & Stores
Shelby Park
9.0 out of 10, Wonderful, (12 reviews)
"Perfect location and house for several people!"
United States
Pam H.
The price is NZ$502
includes taxes & fees
23 Feb - 24 Feb
NEW Cozy Home in Shelby Park | Near Cafes & Stores
Smart TV

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (37 reviews)
"Clean home and very friendly neighbors "
United States
Tranquilina G.
The price is NZ$447
includes taxes & fees
19 Feb - 20 Feb
Close to Everything in Louisville!!!
Exterior

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
8.8 out of 10, Excellent, (8 reviews)
"Stayed for a friends wedding at Whitehall. Location was great and we were able to walk to a handful of restaurants and coffee shops "
United States
Natalie H.
The price is NZ$468
includes taxes & fees
19 Feb - 20 Feb
St. Matthew’s - Walk to Shops & Restaurants
Outdoor dining

The Burnt Barrel | New HotTub & Grill | Backyard!

The Burnt Barrel | New HotTub & Grill | Backyard!
Germantown
10.0 out of 10, Exceptional, (3 reviews)
"Excellent walking to different little shops. Super decorated inside and out. Loved the hot tub. Would stay again! "
United States
kevin m.
The price is NZ$362
includes taxes & fees
22 Feb - 23 Feb
The Burnt Barrel | New HotTub & Grill | Backyard!
Interior

Carriage House, 7 minutes from downtown Louisville

Carriage House, 7 minutes from downtown Louisville
louisville
10.0 out of 10, Exceptional, (52 reviews)
"Clean, quiet, very comfortable. Great shower too. "
United States
Michael D.
The price is NZ$399
includes taxes & fees
11 Feb - 12 Feb
Carriage House, 7 minutes from downtown Louisville
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

Towneplace Suites By Marriott Louisville Downtown

Towneplace Suites By Marriott Louisville Downtown

10/10 Excellent
"Clean and comfortable. Many options for breakfast. Enjoyed the bar/lounge but would have liked it more if small bites were an option. Unsure why the firepit was lit, for the smokers to enjoy a cigarette, but I guess there was a reason."
Kerri 2-night trip
Posted 1 day ago
Towneplace Suites By Marriott Louisville Downtown

Find out more about Charlestown

Charlestown Holiday Homes information

Number of reviews
396
Accommodation
905 Holiday Homes
Lowest Price
NZ$243
Highest Price
NZ$620