A forest path with a metal archway supported by concrete pillars.

Charlestown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Charlestown vacation rentals

A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

1. 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, (24 reviews)
"Amazing, would stay again in a heartbeat"
United States
Ian M.
The price is ￥16,599
￥24,892 total
includes taxes & fees
Sep 21 - Sep 22
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A reception desk with a staff member, a guest, and a child.

2. 1 King Bed|Nsmk,Micfridge

1 King Bed|Nsmk,Micfridge
Jeffersonville
10.0 out of 10, Exceptional, (282 reviews)
"Location's pretty solid, close enough to attractions yet quiet enough for restful nights."
United States
Anonymous traveler
The price is ￥8,494
￥9,598 total
includes taxes & fees
Oct 1 - Oct 2
1 King Bed|Nsmk,Micfridge
A modern living room with a large window overlooking a lake, a sofa with patterned cushions, a glass coffee table, and a lamp.

3. The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville
Louisville
10.0 out of 10, Exceptional, (216 reviews)
"Beautiful location…very relaxing after a busy day!"
United States
Jim N.
The price is ￥28,826
￥57,583 total
includes taxes & fees
Sep 23 - Sep 24
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville
A modern living room with a sofa, coffee table, TV, and wooden cabinet.

4. Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard

Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
Jeffersonville
10.0 out of 10, Exceptional, (8 reviews)
"You won’t regret it! Private parking, quiet neighborhood, and fully stocked supplies for your stay! Easy check in and great hostess!"
United States
Sharonda
The price is ￥18,547
￥39,539 total
includes taxes & fees
Sep 22 - Sep 23
Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
A modern two-story house with a dark exterior, a covered front porch with stone pillars, and a stone pathway leading to the entrance.

5. The Adelyn, where comfort meets convenience

The Adelyn, where comfort meets convenience
Jeffersonville
10.0 out of 10, Exceptional, (9 reviews)
"The host was super responsive. The place was absolutely a gem!"
United States
Jeffery
The price is ￥19,128
￥48,085 total
includes taxes & fees
Sep 22 - Sep 23
The Adelyn, where comfort meets convenience
A modern kitchen with white cabinets, a large island with bar stools, a built-in oven, and a stainless steel refrigerator.

6. Country home with beautiful views and access to hiking, biking, and horse trails

Country home with beautiful views and access to hiking, biking, and horse trails
Henryville
9.8 out of 10, Exceptional, (42 reviews)
"Loved the dog-friendly house that even had a nice small fenced in area. Super quiet and close to the Knobstone trail for some exploring. The house was easy to find and access and the host was friendly. Thanks for the great place to stay!"
United States
Forrest K.
The price is ￥25,596
￥42,741 total
includes taxes & fees
Sep 22 - Sep 23
Country home with beautiful views and access to hiking, biking, and horse trails
A living room with a sectional sofa, a fireplace, a flat-screen TV, and a zebra-patterned chair.

7. Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum Row

Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum Row
Clarksville
8.8 out of 10, Excellent, (10 reviews)
"Was a great time and very clean "
United States
Jeff B.
The price is ￥11,169
￥32,079 total
includes taxes & fees
Sep 21 - Sep 22
Bourbon & Derby 2mile to Whiskey Row Main St Louisville Bourbon City Museum Row
A living room with a glass coffee table, two armchairs, a sofa, a TV, and a bookshelf.

8. Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
New Albany
10.0 out of 10, Exceptional, (51 reviews)
"Nice property, we would stay again"
United States
Allan A.
The price is ￥10,859
￥31,729 total
includes taxes & fees
Sep 30 - Oct 1
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

9. Uptown Class

Uptown Class
New Albany
9.8 out of 10, Exceptional, (36 reviews)
"Communication was good,very responsive"
United States
Jerrel
The price is ￥23,270
￥70,119 total
includes taxes & fees
Sep 28 - Sep 29
Uptown Class
A wooden sauna with benches, a window with a view, and a hanging basket.

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

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (96 reviews)
"Excellent location"
United States
Danielle S.
The price is ￥22,571
￥52,202 total
includes taxes & fees
Sep 29 - Sep 30
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
A brick building with arched windows and a sign reading "The Bellwether."

11. The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.2 out of 10, Wonderful, (57 reviews)
"Check in was easy, very clean and nice. Very unique property!"
United States
Amy
The price is ￥22,443
￥27,172 total
includes taxes & fees
Sep 21 - Sep 22
The Bellwether Hotel
A garden with a stone bench, a decorative dragon statue, and various plants.

12. Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
Crescent Hill
10.0 out of 10, Exceptional, (135 reviews)
"Wonderful experience."
United States
Andrew R.
The price is ￥20,167
￥36,012 total
includes taxes & fees
Sep 22 - Sep 23
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
A modern kitchen with dark cabinetry, a central island, and pendant lighting.

13. Putt Putt House by Louisville Walking Bridge

Putt Putt House by Louisville Walking Bridge
Jeffersonville
10.0 out of 10, Exceptional, (15 reviews)
"The house and location were fantastic! The house had everything we needed and was very thoughtfully supplied."
United States
Emily F.
The price is ￥15,513
￥45,577 total
includes taxes & fees
Sep 21 - Sep 22
Putt Putt House by Louisville Walking Bridge
A rustic cabin interior with a stone fireplace, wooden beams, a green sofa, and a television.

14. Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs

Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs
Floyd knobs
9.6 out of 10, Exceptional, (4 reviews)
"Great spot for a guys weekend."
United States
Fr. Jay H.
The price is ￥24,433
￥31,467 total
includes taxes & fees
Sep 18 - Sep 19
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs
A bedroom with a wooden bed, bedside tables, a nightstand, a window with blinds, and a wall-mounted lamp.

15. Convenient & Cozy! Close to everything Louisville!

Convenient & Cozy! Close to everything Louisville!
Belknap
The price is ￥19,615
￥42,926 total
includes taxes & fees
Sep 21 - Sep 22
Convenient & Cozy! Close to everything Louisville!
A two-story house with a prominent tower, multiple balconies, and a white picket fence.

16. Sunny Side of Whiskey Row 2miles Main Street Louisville Bourbon City, Museum Row

Sunny Side of Whiskey Row 2miles Main Street Louisville Bourbon City, Museum Row
Clarksville
9.4 out of 10, Exceptional, (27 reviews)
"Apartment is very pretty and had everything we needed. Location is perfect!"
United States
Vonya G.
The price is ￥8,377
￥28,749 total
includes taxes & fees
Sep 21 - Sep 22
Sunny Side of Whiskey Row 2miles Main Street Louisville Bourbon City, Museum Row
A modern kitchen with a large window, a dining area with a table and chairs, and a view of the outdoors.

17. Charming house in one of Louisville's most coveted neighborhoods

Charming house in one of Louisville's most coveted neighborhoods
Louisville
10.0 out of 10, Exceptional, (86 reviews)
"Enjoyed the location and quiet neighborhood. You will not be one disappointed."
United States
Tania B.
The price is ￥29,537
￥54,418 total
includes taxes & fees
Sep 23 - Sep 24
Charming house in one of Louisville's most coveted neighborhoods
A two-story house with a porch, a front door, and a small front yard.

18. Stunning Victorian Home - prime location minutes from Louisville

Stunning Victorian Home - prime location minutes from Louisville
Jeffersonville
9.8 out of 10, Exceptional, (30 reviews)
"Clean"
United States
Jason M.
The price is ￥35,680
￥89,927 total
includes taxes & fees
Sep 28 - Sep 29
Stunning Victorian Home - prime location minutes from Louisville
A two-story residential building with a front porch, a wooden door, and a number '414' on the right side.

19. The Curated Chateau—Minutes from Louisville

The Curated Chateau—Minutes from Louisville
New Albany
9.8 out of 10, Exceptional, (47 reviews)
"It was a perfect stay for our weekend at Churchill Downs."
United States
Peggy S.
The price is ￥19,383
￥44,342 total
includes taxes & fees
Sep 21 - Sep 22
The Curated Chateau—Minutes from Louisville

20. Riverside Suite: Walk to Big Four Bridge &

Riverside Suite: Walk to Big Four Bridge &
Jeffersonville
9.6 out of 10, Exceptional, (44 reviews)
"Awesome little spot "
United States
Paul G.
The price is ￥7,757
￥22,975 total
includes taxes & fees
Sep 22 - Sep 23
Riverside Suite: Walk to Big Four Bridge &
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

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

10/10 Excellent
"Room was clean and quiet"
Patricia 1-night trip
Posted 1 hour ago
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

Find out more about Charlestown

Search for holiday rentals in Charlestown on Expedia! You can easily find your home rentals, villas, holiday apartments in Charlestown using one of the methods below:

  • View our selection of featured holiday rentals in Charlestown
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  • Enter your travel dates to view the best deals on holiday rentals in Charlestown while they last

Look no further and take a look at our great range of rental properties in Charlestown!

Frequently asked questions

Are there vacation rentals in Charlestown?

Yes, we give you a choice of vacation rentals in Charlestown close to Charlestown Family Activities Park, or you can choose a more remote option if you'd like a relaxing place to stay. Charlestown is known for its riverfront.

What are some of the best vacation home rentals that Charlestown has to offer?

Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly: This vacation home rental outside of Charlestown offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Charlestown?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Charlestown stay.

What can I see and do in Charlestown?

Ohio River Valley and Woodford Farms Family Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Charlestown Family Activities Park. Other places in town to visit include Charlestown State Park and Rose Island.

What are vacation rentals like in Charlestown?

Vacation rentals are private properties you can stay in for a short or long stay in Charlestown. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.