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Holiday Homes in Charlestown

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Charlestown

Big Chill! 5br 2ba Walkable- Hot tub!
Terrace/patio

Big Chill! 5br 2ba Walkable- Hot tub!

2.0 star property
9.4 out of 10, Exceptional, (10)
"Everything was just like it said in description. Great property for my work stay. "
Big Chill! 5br 2ba Walkable- Hot tub!
The Chestnut - Nulu
Terrace/patio

The Chestnut - Nulu

2.0 star property
9.8 out of 10, Exceptional, (20)
"We stayed here for a "
The price is AU$301
includes taxes & fees
6 Aug - 7 Aug
The Chestnut - Nulu
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
Fridge, microwave, oven, stovetop

New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

9.8 out of 10, Exceptional, (20)
"Clean fantastic property, great communication, easy walk to Churchill Downs!"
The price is AU$346
includes taxes & fees
31 Aug - 1 Sept
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
Wanderlust - Hot tub / fire pit - Location!
Outdoor spa tub

Wanderlust - Hot tub / fire pit - Location!

10.0 out of 10, Exceptional, (4)
"4 guys in our group. We all had big comfy beds and enjoyed the hot tub and fire pit outside. Would recommend!"
Wanderlust - Hot tub / fire pit - Location!
Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly
Microwave, oven, stovetop, dishwasher

Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly

10.0 out of 10, Exceptional, (1)
"This post will be long. My family and I were completely surprised by the beauty of this property. The intentionality of the bedrooms, interior decorations, the size of the property , so we all could stretch out. I am thoroughly impressed. We will be back."
Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly
The Caldwell - Germantown Highlands
Fridge, microwave, oven, stovetop

The Caldwell - Germantown Highlands

10.0 out of 10, Exceptional, (27)
"Nice house for our weekend stay. We would book again! "
The price is AU$301
includes taxes & fees
11 Aug - 12 Aug
The Caldwell - Germantown Highlands
Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly
Fridge, microwave, oven, stovetop

Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly

10.0 out of 10, Exceptional, (136)
"The property is fabulous! Our group absolutely loved the stay. we liked the property so much that we found ourselves cutting our visits throughout Kentucky short to get back to the house to enjoy the accommodation. "
Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly
Newly Renovated Studio! Ideal location for walking to restaurants & shops
Fridge, microwave, oven, stovetop

Newly Renovated Studio! Ideal location for walking to restaurants & shops

9.8 out of 10, Exceptional, (39)
"My teenage daughter and I stayed here for a volleyball tournament that was held at KICC. The location was perfect. Very short drive to the courts and many restaurants and stores were walkable from the house. Close to the airport too. This was perfect for our needs. "
Newly Renovated Studio! Ideal location for walking to restaurants & shops
Close to Everything in Louisville!!!
Exterior detail

Close to Everything in Louisville!!!

9.2 out of 10, Wonderful, (32)
"Very clean and nice place close to the exposition center would stay there again."
The price is AU$428
includes taxes & fees
6 Aug - 7 Aug
Close to Everything in Louisville!!!
Family Friendly, Historic Mansion Row, **5 min from Louisville!**
Lobby

Family Friendly, Historic Mansion Row, **5 min from Louisville!**

10.0 out of 10, Exceptional, (38)
"Convent and accommodation was excellent for 10 "
Family Friendly, Historic Mansion Row, **5 min from Louisville!**
3 BR Downtown Sanctuary! Huge back yard
TV, offices

3 BR Downtown Sanctuary! Huge back yard

8.8 out of 10, Excellent, (36)
"House was very nice"
The price is AU$375
includes taxes & fees
6 Aug - 7 Aug
3 BR Downtown Sanctuary! Huge back yard
Ultra Modern in NuLu, Hot Tub, Fire Pit, King Bed
Terrace/patio

Ultra Modern in NuLu, Hot Tub, Fire Pit, King Bed

9.8 out of 10, Exceptional, (55)
"Great property and wonderful hosts. Very comfortable and relaxing place in a great location. "
The price is AU$698
includes taxes & fees
13 Aug - 14 Aug
Ultra Modern in NuLu, Hot Tub, Fire Pit, King Bed
Charming shotgun home, minutes from Churchill Downs, Expo Center & downtown
Outdoor dining

Charming shotgun home, minutes from Churchill Downs, Expo Center & downtown

9.8 out of 10, Exceptional, (32)
"House was clean and very nice. Description online was accurate and we enjoyed our stay very much!"
Charming shotgun home, minutes from Churchill Downs, Expo Center & downtown
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Property grounds

The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands

10.0 out of 10, Exceptional, (157)
"We loved this house, location and host! We would stay again."
The price is AU$524
includes taxes & fees
6 Aug - 7 Aug
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Relaxing 4BR Haven by CozySuites
Fridge, microwave, oven, stovetop

Relaxing 4BR Haven by CozySuites

Relaxing 4BR Haven by CozySuites
New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!
TV, table football, offices

New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!

9.4 out of 10, Exceptional, (27)
"Great location and awesome place to stay. We all had a great time!"
New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!
Equus: Work Friendly & Near Downtown
Dining

Equus: Work Friendly & Near Downtown

9.0 out of 10, Wonderful, (4)
"Great location!"
Equus: Work Friendly & Near Downtown
DERBY CITY SPEAKEASY 3-story 4-bedroom Historic Mansion 2 mi to Whiskey Row-NULU
Fridge, microwave, oven, stovetop

DERBY CITY SPEAKEASY 3-story 4-bedroom Historic Mansion 2 mi to Whiskey Row-NULU

10.0 out of 10, Exceptional, (81)
"House is gorgeous. Proximity to downtown is great. Owners were very communicative and helpful. Can’t find anything bad to say at all. "
The price is AU$767
includes taxes & fees
7 Aug - 8 Aug
DERBY CITY SPEAKEASY 3-story 4-bedroom Historic Mansion 2 mi to Whiskey Row-NULU
Spectacular waterfront house!
Outdoor spa tub

Spectacular waterfront house!

9.6 out of 10, Exceptional, (77)
"We had a great time and loved the view of the river! "
Spectacular waterfront house!
Kentucky holiday home with Hot Tub & pool In Louisville KY
Fridge, microwave, oven, stovetop

Kentucky holiday home with Hot Tub & pool In Louisville KY

9.0 out of 10, Wonderful, (22)
"Very nice house, plenty of space. Nice quite neighborhood, short drive to attractions & activities. "
Kentucky holiday home with Hot Tub & pool In Louisville KY
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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