Photo by Mark Wilcoxson

Search Vacation Homes in Charlestown

Check prices for these dates

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

Vacation Homes in Charlestown

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!
Home In The Highlands! 5br/2ba Walkable! Hot tub!
Outdoor dining

Home In The Highlands! 5br/2ba Walkable! Hot tub!

9.4 out of 10, Exceptional, (11)
"Great location and beautiful home"
Home In The Highlands! 5br/2ba Walkable! Hot tub!
✪Heated Pool, Firepit, Bikes, Grill, Pets✪
Fridge, microwave, oven, stovetop

✪Heated Pool, Firepit, Bikes, Grill, Pets✪

8.8 out of 10, Excellent, (14)
"Thank you for sharing your lovely home with us. The pool was a hit with the kids and we had a wonderful time relaxing and enjoying our vacation. Thank you for being such gracious hosts and providing us with a comfortable and enjoyable stay. We hope to visit again in the future!"
$291 nightly
The price is $333
Aug 10 - Aug 11
Total includes taxes and fees
✪Heated Pool, Firepit, Bikes, Grill, Pets✪
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
6000SF~Louisville~Sleeps24~LawnOasis~Dome~HotTub~Pets~Firepit~Lux Amenities~View
Outdoor dining

6000SF~Louisville~Sleeps24~LawnOasis~Dome~HotTub~Pets~Firepit~Lux Amenities~View

2.5 star property
10.0 out of 10, Exceptional, (12)
"We had a great time- the property was perfect for our group of 14. Would stay here again!"
$1,608 nightly
The price is $1,871
Aug 24 - Aug 25
Total includes taxes and fees
6000SF~Louisville~Sleeps24~LawnOasis~Dome~HotTub~Pets~Firepit~Lux Amenities~View
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."
$239 nightly
The price is $277
Aug 9 - Aug 10
Total includes taxes and fees
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!**
New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!
TV, foosball, 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!
Highlands Derby City Dream ~ 6BR+Hot Tub Sleep 14
Terrace/patio

Highlands Derby City Dream ~ 6BR+Hot Tub Sleep 14

10.0 out of 10, Exceptional, (15)
"This place was perfect for our group. We had 6 couples stay and it was such a great location. It is close to so many things to do and the grocery store is right behind the house. Would definitely stay here again."
$696 nightly
The price is $796
Aug 10 - Aug 11
Total includes taxes and fees
Highlands Derby City Dream ~ 6BR+Hot Tub Sleep 14
The Chuckwick House - Sleeps 10 in Beds
Terrace/patio

The Chuckwick House - Sleeps 10 in Beds

9.4 out of 10, Exceptional, (32)
"Great location for visiting all the distilleries in the area."
The Chuckwick House - Sleeps 10 in Beds
3 BR, 2.5 Baths! GREAT VALUE!!! LOCATION!!! Highlands, EXPO, Downtown, NULU
Outdoor dining

3 BR, 2.5 Baths! GREAT VALUE!!! LOCATION!!! Highlands, EXPO, Downtown, NULU

9.8 out of 10, Exceptional, (175)
"Overall a great place to stay."
$284 nightly
The price is $329
Aug 11 - Aug 12
Total includes taxes and fees
3 BR, 2.5 Baths! GREAT VALUE!!! LOCATION!!! Highlands, EXPO, Downtown, NULU
3-story Bourbon Luxe Historic Retreat 2 mi to Whiskey Row-NULU
Fridge, microwave, oven, stovetop

3-story Bourbon Luxe Historic Retreat 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. "
$424 nightly
The price is $492
Aug 10 - Aug 11
Total includes taxes and fees
3-story Bourbon Luxe Historic Retreat 2 mi to Whiskey Row-NULU
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!
Relaxing Country Getaway
Interior

Relaxing Country Getaway

9.4 out of 10, Exceptional, (34)
"Wonderful stay, very private. Cozy place perfect for couples looking to unwind. Would stay again."
Relaxing Country Getaway
Kentucky holiday home with Hot Tub & pool In Louisville KY
Fridge, microwave, oven, stovetop

Kentucky holiday home with Hot Tub & pool In Louisville KY

9.2 out of 10, Wonderful, (23)
"Very nice house, plenty of space. Nice quite neighborhood, short drive to attractions & activities. "
Kentucky holiday home with Hot Tub & pool In Louisville KY
Best Location!!! - Huge Historic Charm - 3BR-3BTH
3 bedrooms, iron/ironing board, WiFi

Best Location!!! - Huge Historic Charm - 3BR-3BTH

9.2 out of 10, Wonderful, (85)
"Very accommodating & clean. "
Best Location!!! - Huge Historic Charm - 3BR-3BTH
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. "
$381 nightly
The price is $442
Aug 13 - Aug 14
Total includes taxes and fees
Ultra Modern in NuLu, Hot Tub, Fire Pit, King Bed
Luxury victorian house 8BD 3.5Bth Game yard
Fridge, microwave, oven, stovetop

Luxury victorian house 8BD 3.5Bth Game yard

10.0 out of 10, Exceptional, (1)
"House is newly remodeled and sleeps many comfortably. We loved the back yard hangout and party games. Location is excellent. Walking distance to a fun restaurant/bar scene. The host, Michael, was very responsive. Would definitely stay again. "
Luxury victorian house 8BD 3.5Bth Game yard
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
New! Welcome to the Jungle, Baby! 3br2ba Hot Tub!
Fridge, microwave, oven, stovetop

New! Welcome to the Jungle, Baby! 3br2ba Hot Tub!

8.8 out of 10, Excellent, (9)
"Great experience "
New! Welcome to the Jungle, Baby! 3br2ba Hot Tub!
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.
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

La Quinta Inn & Suites by Wyndham Louisville NE/Old Henry Rd

La Quinta Inn & Suites by Wyndham Louisville NE/Old Henry Rd

10/10 Excellent
"Very nice, clean, affordable stay "
Kyla 4-night trip
Posted 20 hours ago
La Quinta Inn & Suites by Wyndham Louisville NE/Old Henry Rd