Holiday Homes in Charlestown

  • 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
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

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, (19 reviews)
"House was cozy, and host was responsive. Rooms were clean and welcoming. A lovely place to stay."
United States
Alec S.
The price is NZ$273
includes taxes & fees
8 June - 9 June
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Interior

Emerald Lake Retreat Charlestown

Emerald Lake Retreat Charlestown
Charlestown
10.0 out of 10, Exceptional, (3 reviews)
"Roomy, clean, nice setting in nice neighborhood."
United States
David P.
The price is NZ$742
includes taxes & fees
19 May - 20 May
Emerald Lake Retreat Charlestown
Dining

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Jeffersontown
9.6 out of 10, Exceptional, (32 reviews)
"We had a wonderful experience. The house was great and had everything we needed. Everything was clean and well maintained. The host was very friendly, responsive, and flexible, which we really appreciated. Would definitely stay again!"
United States
Dieudonne N.
The price is NZ$1,219
includes taxes & fees
14 May - 15 May
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Dining

3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms

3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms
La Grange
10.0 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay!"
United States
Katie H.
The price is NZ$1,455
includes taxes & fees
17 May - 18 May
3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms
Terrace/patio

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (89 reviews)
"Very nice place"
United States
Seth B.
The price is NZ$549
includes taxes & fees
18 May - 19 May
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Outdoor dining

T&E Riverhouse Retreat

T&E Riverhouse Retreat
Hanover
10.0 out of 10, Exceptional, (6 reviews)
"Relaxing, quite, clean, comfortable, great view!"
United States
Heather R.
The price is NZ$666
includes taxes & fees
18 May - 19 May
T&E Riverhouse Retreat
Exterior

NEW Pet Friendly, WiFi, Bourbon Trail, Downtown Local Dining, Fully Loaded

NEW Pet Friendly, WiFi, Bourbon Trail, Downtown Local Dining, Fully Loaded
Prospect
10.0 out of 10, Exceptional, (13 reviews)
"Great home, excellent location, easy communication with the host-looking forward to a return trip!"
United States
Kurt F.
The price is NZ$1,263
includes taxes & fees
14 May - 15 May
NEW Pet Friendly, WiFi, Bourbon Trail, Downtown Local Dining, Fully Loaded
Interior

Cozy Cottage on Spring---Centrally Located and 10 mins from downtown Louisville

Cozy Cottage on Spring---Centrally Located and 10 mins from downtown Louisville
New Albany
10.0 out of 10, Exceptional, (56 reviews)
"This house was perfect and Molly is an exceptional host! "
United States
Julie T.
The price is NZ$705
includes taxes & fees
25 May - 26 May
Cozy Cottage on Spring---Centrally Located and 10 mins from downtown Louisville
Fridge, microwave, oven, stovetop

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE
Louisville
10.0 out of 10, Exceptional, (83 reviews)
"Host was accommodating and welcoming. "
United States
Bobbie S.
The price is NZ$409
includes taxes & fees
25 May - 26 May
Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE
Miscellaneous

Charming 3BR w Large Yard Walk to Downtown

Charming 3BR w Large Yard Walk to Downtown
Jeffersonville
9.6 out of 10, Exceptional, (29 reviews)
"We enjoyed our stay"
United States
Jennifer L.
The price is NZ$936
includes taxes & fees
20 May - 21 May
Charming 3BR w Large Yard Walk to Downtown
Exterior

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Louisville
9.8 out of 10, Exceptional, (81 reviews)
"We brought a large group to a conference in Louisville and it was perfect to have all of us stay together. It was a historic house, full of charm. Only negative was the warm water ran out quickly with so many people."
United States
Benjamin T.
The price is NZ$2,088
includes taxes & fees
18 May - 19 May
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Interior

⭐Fully fenced yard⭐4 car driveway⭐firepit⭐central location⭐basement⭐

⭐Fully fenced yard⭐4 car driveway⭐firepit⭐central location⭐basement⭐
Avondale Melbourne Heights
9.6 out of 10, Exceptional, (51 reviews)
"Great hosts, good location for our family member, everything very nice!"
United States
Elizabeth F.
The price is NZ$737
includes taxes & fees
19 May - 20 May
⭐Fully fenced yard⭐4 car driveway⭐firepit⭐central location⭐basement⭐
Interior

Victorian Center Jeffersonville

Victorian Center Jeffersonville
Jeff
9.4 out of 10, Exceptional, (55 reviews)
"House was beautiful! We were in town for the Kentucky Derby, so everything was higher than normal, but this house was still reasonable compared to others. Location was great! Nice neighborhood within walking distance to restaurants and the river. Very peaceful and not at all concerned with safety. The upstairs suite was huge! Tons of room and everything we needed."
United States
Randi
The price is NZ$549
includes taxes & fees
14 May - 15 May
Victorian Center Jeffersonville
Fridge, microwave, oven, stovetop

Uptown Class

Uptown Class
New Albany
9.8 out of 10, Exceptional, (19 reviews)
"Great property. Good location. "
United States
Damont P.
The price is NZ$691
includes taxes & fees
17 May - 18 May
Uptown Class
Exterior

Stunning Victorian Home - prime location minutes from Louisville

Stunning Victorian Home - prime location minutes from Louisville
Jeffersonville
9.8 out of 10, Exceptional, (27 reviews)
"We really enjoyed our stay. Close to everything!"
United States
cheryl n.
The price is NZ$961
includes taxes & fees
21 May - 22 May
Stunning Victorian Home - prime location minutes from Louisville
Smart TV

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (39 reviews)
"This is a great little place to stay! Close to the Exposition Center and a lot of other attractions. It is an older place but clean and comfortable. This is our second stay at this place. "
United States
jaggers959
The price is NZ$450
includes taxes & fees
17 May - 18 May
Close to Everything in Louisville!!!
Fridge, microwave, oven, stovetop

Minutes from Churchill Downs & Downtown Lou!

Minutes from Churchill Downs & Downtown Lou!
Schnitzelburg
10.0 out of 10, Exceptional, (9 reviews)
"Met my brother there for the weekend. Great food just 2 blocks away. Very happy with our stay. We would stay there again!"
United States
Greg B.
The price is NZ$597
includes taxes & fees
14 May - 15 May
Minutes from Churchill Downs & Downtown Lou!
Exterior

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

LUX Waterside Retreat with Geo Dome + Outdoor Fire Table, Historic Property
Prospect
9.8 out of 10, Exceptional, (10 reviews)
"Loved my stay, just want I needed. Went to the music festival and bought some really cool boots, I’ll be back!"
United States
Robert C.
LUX Waterside Retreat with Geo Dome + Outdoor Fire Table, Historic Property
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$766
includes taxes & fees
17 May - 18 May
The Sweet Retreat Wheelchair Accessible Historic Home
Property grounds

Spectacular waterfront house!

Spectacular waterfront house!
Prospect
9.6 out of 10, Exceptional, (92 reviews)
"The home was great, the host was very responsive."
United States
jasmine p.
The price is NZ$911
includes taxes & fees
9 June - 10 June
Spectacular waterfront house!
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

2/10 Terrible
"I arrived to check in at 6:00 pm and stood in line for 30 minutes only to be told my room wasn’t ready but would be ready in 45 minutes. An hour and half later at 8:10 I went back to the front desk to be told it still wasn’t ready. At 8:45 I finally received keys to the room only to arrive at the room to find it’s not the room I reserved. I reserved a junior presidential suite with a king bed but got put in a double bed suite. There was also a dirty towel left hanging on the back of the bathroom door. The only compensation offered for all of this was free breakfast which we couldn’t even use. The experience was extremely frustrating and below par to say the least."
Heather 2-night trip
Posted 1 hour ago
Crowne Plaza Louisville Airport Expo Ctr by IHG

Find out more about Charlestown

Charlestown Holiday Homes information

Number of reviews
539
Accommodation
935 Holiday Homes
Lowest Price
NZ$273
Highest Price
NZ$2,088