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Our top choices for Charlestown vacation homes

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 ¥17,154
¥25,666 total
includes taxes & fees
Jun 15 - Jun 16
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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 ¥17,498
¥71,361 total
includes taxes & fees
May 21 - May 22
Emerald Lake Retreat Charlestown

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 ¥42,790
¥73,971 total
includes taxes & fees
May 24 - May 25
The Sweet Retreat Wheelchair Accessible Historic Home

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 ¥85,597
¥201,967 total
includes taxes & fees
Jun 10 - Jun 11
3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms

Near Highways and a 20 Min Drive to Louisville's Main Attractions

Near Highways and a 20 Min Drive to Louisville's Main Attractions
Louisville
10.0 out of 10, Exceptional, (53 reviews)
"Great place!"
United States
Nakoma F.
The price is ¥25,016
¥58,902 total
includes taxes & fees
Jun 1 - Jun 2
Near Highways and a 20 Min Drive to Louisville's Main Attractions

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 ¥36,348
¥62,811 total
includes taxes & fees
Jun 8 - Jun 9
T&E Riverhouse Retreat

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 ¥57,036
¥117,820 total
includes taxes & fees
May 21 - May 22
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
10.0 out of 10, Exceptional, (15 reviews)
"Very nice facility and relaxing setting . "
United States
Robert V.
The price is ¥10,947
¥29,409 total
includes taxes & fees
May 27 - May 28
Modern cabin very close to scenic riverfront walks

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 ¥30,019
¥39,269 total
includes taxes & fees
May 26 - May 27
Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE

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 ¥107,210
¥205,186 total
includes taxes & fees
May 26 - May 27
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

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 ¥58,648
¥121,959 total
includes taxes & fees
May 26 - May 27
NEW Pet Friendly, WiFi, Bourbon Trail, Downtown Local Dining, Fully Loaded

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, (11 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.
The price is ¥22,677
¥61,034 total
includes taxes & fees
May 25 - May 26
LUX Waterside Retreat with Geo Dome + Outdoor Fire Table, Historic Property

⭐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, (52 reviews)
"Great hosts, good location for our family member, everything very nice!"
United States
Elizabeth F.
The price is ¥29,428
¥75,329 total
includes taxes & fees
May 27 - May 28
⭐Fully fenced yard⭐4 car driveway⭐firepit⭐central location⭐basement⭐

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 ¥43,678
¥88,859 total
includes taxes & fees
Jun 9 - Jun 10
Spectacular waterfront house!

Lumos Stays: 65" 4K TV, memory foam, kid-friendly

Lumos Stays: 65" 4K TV, memory foam, kid-friendly
Bon Air
10.0 out of 10, Exceptional, (5 reviews)
"Very close to grocery stores, restaurants and the zoo. This house was just what we needed. "
United States
Gail S.
The price is ¥20,673
¥52,059 total
includes taxes & fees
Jun 15 - Jun 16
Lumos Stays: 65" 4K TV, memory foam, kid-friendly

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (10 reviews)
"It was everything we needed."
United States
Carmen C.
The price is ¥12,169
¥63,054 total
includes taxes & fees
May 31 - Jun 1
St. Matthew’s - Walk to Shops & Restaurants

Derby Favorite! Spacious 4BR Near Churchill Downs

Derby Favorite! Spacious 4BR Near Churchill Downs
Rockcreek Lexington Road
9.4 out of 10, Exceptional, (6 reviews)
"Fantastic service. The home was beautiful and if in town again we would definitely stay there again. Nice area great access to amenities. "
United States
T J.
The price is ¥27,331
¥57,002 total
includes taxes & fees
May 27 - May 28
Derby Favorite! Spacious 4BR Near Churchill Downs

The Jungalow: 65" 4K TV, memory foam, kid-friendly

The Jungalow: 65" 4K TV, memory foam, kid-friendly
Bon Air
9.8 out of 10, Exceptional, (21 reviews)
"It was a great day. The host was very accommodating and friendly. Definitely would love to stay again!!"
United States
Cassie B.
The price is ¥25,841
¥60,089 total
includes taxes & fees
Jun 2 - Jun 3
The Jungalow: 65" 4K TV, memory foam, kid-friendly

Historic Cottage with modern amenities

Historic Cottage with modern amenities
louisville
9.4 out of 10, Exceptional, (27 reviews)
"Perfect place for our short stay in Louisville! Very nice neighborhood and cozy cottage! "
United States
Adrienne H.
The price is ¥35,737
¥62,681 total
includes taxes & fees
May 21 - May 22
Historic Cottage with modern amenities

Carriage House, 7 minutes from downtown Louisville

Carriage House, 7 minutes from downtown Louisville
louisville
10.0 out of 10, Exceptional, (56 reviews)
"Amazing host! Great place to stay."
United States
Robert M.
The price is ¥23,825
¥41,481 total
includes taxes & fees
Jun 8 - Jun 9
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

Find out more about Charlestown

Charlestown Vacation Homes information

Number of reviews
528
Accommodation
867 Vacation Homes
Lowest Price
¥25,666
Highest Price
¥205,186