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Charlestown Vacation Rentals

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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

Browse Select Charlestown Vacation Homes

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✪
Kitchen features a range hood, oven, microwave, toaster, and slow cooker, with a tiled backsplash and window above the sink.

✪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!"
The price is CA $119
CA $415 total
includes taxes & fees
Aug 11 - Aug 12
✪Heated Pool, Firepit, Bikes, Grill, Pets✪
Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly
Enjoy cooking in this well-equipped kitchen with a central island, gas stove, and oven.

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
Enjoy a peaceful evening by the fire pit in the backyard with a unique dome structure and mature trees.

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!"
The price is CA $1,167
CA $2,552 total
includes taxes & fees
Aug 24 - Aug 25
6000SF~Louisville~Sleeps24~LawnOasis~Dome~HotTub~Pets~Firepit~Lux Amenities~View
Close to Everything in Louisville!!!
Stylish single-story home with a charming front porch and lush surroundings.

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 CA $158
CA $391 total
includes taxes & fees
Aug 17 - Aug 18
Close to Everything in Louisville!!!
Family Friendly, Historic Mansion Row, **5 min from Louisville!**
Experience grandeur in this opulent space with tall columns, a large mirror, and a stunning chandelier.

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!
Relax in this inviting living room with a fireplace, leather sofas, and a flat-screen TV.

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
Relax in this serene outdoor patio with a fire feature, perfect for dining or socializing with friends and family.

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."
The price is CA $364
CA $1,094 total
includes taxes & fees
Aug 11 - Aug 12
Highlands Derby City Dream ~ 6BR+Hot Tub Sleep 14
The Chuckwick House - Sleeps 10 in Beds
Relax on the inviting porch with a wicker chair and small bench, surrounded by classic stone walls and a picket fence.

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
Enjoy a patio with a glass table and metal chairs, surrounded by a charming garden and a beautiful house with a front door and porch.

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."
The price is CA $178
CA $452 total
includes taxes & fees
Aug 11 - Aug 12
3 BR, 2.5 Baths! GREAT VALUE!!! LOCATION!!! Highlands, EXPO, Downtown, NULU
3-story Bourbon Luxe Historic Retreat 2 mi to Whiskey Row-NULU
Enjoy cooking in this well-equipped kitchen with a sink, stainless steel refrigerator, and microwave.

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. "
The price is CA $325
CA $676 total
includes taxes & fees
Aug 10 - Aug 11
3-story Bourbon Luxe Historic Retreat 2 mi to Whiskey Row-NULU
Big Chill! 5br 2ba Walkable- Hot tub!
Relax in the hot tub surrounded by a deck and seating area.

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
Cozy space with a fireplace, leather sofa, and wooden panel walls, perfect for relaxing.

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
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, stove, oven, and sink.

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
Cozy bedroom with a neatly made bed, wooden headboard, and a reading nook with a lamp and vase of flowers.

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
Relax in the backyard hot tub, surrounded by a deck and outdoor seating.

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

9.8 out of 10, Exceptional, (56)
"Great property and wonderful hosts. Very comfortable and relaxing place in a great location. "
The price is CA $186
CA $608 total
includes taxes & fees
Aug 13 - Aug 14
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
Kitchen features a large island with a granite countertop, double oven, and microwave.

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!
Enjoy cooking in this kitchen with sleek cabinetry, a refrigerator, microwave, and double oven.

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.
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Top Charlestown Hotel Reviews

Holiday Inn Express & Suites Louisville Downtown by IHG

Holiday Inn Express & Suites Louisville Downtown by IHG

10/10 Excellent
"The shower foot rest was cracked and I really wanted it to shave my legs but they were nice and I reported it. My desk clerk is/ was so nice and friendly-love her help with our questions and needs. May even stay here on our return trip. Plus already recommended to my sister."
Ann 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Louisville Downtown by IHG