Charlestown Rentals

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110 Houses

24

5BR ‘Governor’s Mansion’ Near Louisville

Indiana / Charlestown

Charlestown house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$399

Responds fast!
avg. 10 minutes

Price per night from

$399

15

Charlestown Holiday Apartment 25171

Indiana / Charlestown

Charlestown house

1 1 3 nights min

  • 1 bedroom
  • sleeps 1
  • 3 nights min
  • Air conditioning

Price per night from

$110

Price per night from

$110

24

1BR ‘Governor’s Mansion Overlook’ Near Louisville!

Indiana / Charlestown

Charlestown apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$95

Responds fast!
avg. 10 minutes

Price per night from

$95

Great rentals within 20 miles that match your search

Distance approx 9.8 km from Charlestown

(11) Excellent 

21

Awesome home in the heart of Bluegrass Country!

Kentucky / Louisville

Louisville house

5 13 2 nights min

  • 5 bedrooms
  • sleeps 13
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning
“Perfect relaxing stay during an activity-filled weekend” Wendy is wonderful to work with, and makes sure everything is taken care of that you could possibly need for a great stay. The house is spacious and relaxing, and even though we had 8 people st
…see more

Price per night from

$495

Responds fast!
avg. 1 hour 54 minutes

Price per night from

$495

Distance approx 13.43 km from Charlestown

29

Underwood Home w/40 Acres, Fire Pit & Private Lake

Indiana / Scottsburg

Scottsburg log cabin

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$525

Responds fast!
avg. 40 minutes

Price per night from

$525

Distance approx 14.51 km from Charlestown

(1) Excellent 

5

Carriage House, First Floor

Kentucky / Louisville

Louisville house

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$324

Price per night from

$324

Distance approx 15.83 km from Charlestown

13

Beautiful Victorian Louisville Home

Kentucky / Louisville

Louisville house

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Child Friendly
  • Ask about pets

Price per night from

$447

Responds fast!
avg. 43 minutes

Price per night from

$447

Distance approx 19.16 km from Charlestown

25

Louisville Home w/Fire Pit-Min to Churchill Downs

Kentucky / Louisville

Louisville house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$135

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$135

Distance approx 14.51 km from Charlestown

10

Historic Mansion in Cherokee Triangle

Kentucky / Louisville

Louisville house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$2,287

Price per night from

$2,287

Distance approx 14.54 km from Charlestown

11

Cherokee Rd Condo #1

Kentucky / Louisville

Louisville apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$250

Price per night from

$250

Distance approx 13.2 km from Charlestown

24

NEW! Louisville Home - 7 Miles to Churchill Downs!

Kentucky / Louisville

Louisville house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$150

Responds fast!
avg. 11 minutes

Price per night from

$150

Distance approx 13.01 km from Charlestown

9

Louisville Short Term Condo Rentals

Kentucky / Saint Matthews

Saint Matthews condo

1 3 30 nights min

  • 1 bedroom
  • sleeps 3
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$60

Price per night from

$60

Distance approx 16.06 km from Charlestown

(1) Excellent 

13

GERMANTOWN GEM CLOSE TO EVERYTHING DERBY!

Kentucky / Louisville

Louisville house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$352

Price per night from

$352

Distance approx 14.52 km from Charlestown

(2) Excellent 

15

Penthouse Apartment

Kentucky / Louisville

Louisville apartment

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 3 mi
  • Child Friendly
  • Car not necessary

Price per night from

$290

Price per night from

$290

Distance approx 16.27 km from Charlestown

5

Brand New 2 Bedroom Townhouse

Kentucky / Middletown

Middletown townhouse

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Air conditioning
  • Private garden

Price per night from

$1,905

Price per night from

$1,905

Distance approx 16.36 km from Charlestown

19

Kentucky Home In Derby City

Kentucky / Louisville

Louisville house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$150

Responds fast!
avg. 15 minutes

Price per night from

$150

Distance approx 13.29 km from Charlestown

(2) Excellent 

21

Quiet & safe 2 bed 1 bath in Crescent Hill

Kentucky / Louisville

Louisville apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$130

Responds fast!
avg. 22 minutes

Price per night from

$130

Distance approx 13.29 km from Charlestown

28

Brand New Boutique Getaway

Kentucky / Louisville

Louisville apartment

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$699

Responds fast!
avg. 28 minutes

Price per night from

$699

Distance approx 12.14 km from Charlestown

40

Sunny Side of Louisville

Indiana / Jeffersonville

Jeffersonville house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$1,000

Price per night from

$1,000

Distance approx 11.14 km from Charlestown

67

Deluxe Condo for Derby KY 2018

Indiana / Floyds Knobs

Floyds Knobs condo

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$2,500

Price per night from

$2,500

Distance approx 14.22 km from Charlestown

32

Kentucky Derby House Rental

Kentucky / Louisville

Louisville house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$1,800

Price per night from

$1,800

Distance approx 13.07 km from Charlestown

(1) Excellent 

13

Close To Downtown In Historic Crecent Hill

Kentucky / Louisville

Louisville house

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$348

Responds fast!
avg. 9 minutes

Price per night from

$348

Distance approx 14.95 km from Charlestown

4

Home rental

Kentucky / Louisville

Louisville house

3 9 3 nights min

  • 3 bedrooms
  • sleeps 9
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$493

Price per night from

$493

Distance approx 14.52 km from Charlestown

8

Historic Home in Amazing Location

Kentucky / Louisville

Louisville house

4 6 1 night min

  • 4 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$796

Price per night from

$796

Distance approx 14.47 km from Charlestown

45

4th Street Live at Your Doorstep!

Kentucky / Louisville

Louisville apartment

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$75

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$75

Distance approx 14.47 km from Charlestown

46

Modern Studio in the Heart of Downtown High Rise

Kentucky / Louisville

Louisville apartment

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$75

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$75

Distance approx 14.47 km from Charlestown

49

Downtown High Rise Condo with Rooftop 360 City View!

Kentucky / Louisville

Louisville apartment

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$75

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$75

Distance approx 11.24 km from Charlestown

17

Derby Apartment

Kentucky / Louisville

Louisville apartment

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$59

Price per night from

$59

Distance approx 14.47 km from Charlestown

49

In the Heart of 4th Street Live Festivities!

Kentucky / Louisville

Louisville apartment

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$75

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$75

Distance approx 14.47 km from Charlestown

43

Live Like a Louisville Native - High Rise Apartment

Kentucky / Louisville

Louisville apartment

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$75

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$75

Distance approx 14.04 km from Charlestown

6

Kentucky charm meets modern luxury 2 bed/2 bath loft

Kentucky / Louisville

Louisville apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$325

Responds fast!
avg. 3 hours 38 minutes

Price per night from

$325

Distance approx 14.47 km from Charlestown

43

Stylish Condo Just Minutes from Louisville Yum Center!

Kentucky / Louisville

Louisville apartment

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$75

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$75

Distance approx 14.47 km from Charlestown

29

Newly Renovated High-Rise Downtown Louisville Rental

Kentucky / Louisville

Louisville apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$75

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$75

Distance approx 14.96 km from Charlestown

10

Charming Kentucky Derby rental

Kentucky / Louisville

Louisville house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$1,368

Price per night from

$1,368

Distance approx 14.47 km from Charlestown

36

High-rise Rental in Downtown Louisville!

Kentucky / Louisville

Louisville apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$75

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$75

Distance approx 17.1 km from Charlestown

11

Wooded Retreat PLUS Derby

Kentucky / Louisville

Louisville house

5 14 4 nights min

  • 5 bedrooms
  • sleeps 14
  • 4 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$1,500

Price per night from

$1,500

Distance approx 16.1 km from Charlestown

4

Kentucky Derby Victorian Room in Victorian Farmhouse Old Louisville

Kentucky / Louisville

Louisville room

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child Friendly

Price per night from

$500

Price per night from

$500

Distance approx 14.03 km from Charlestown

6

Spend Easter,Thunder Over Louisville, or KY Derby weekend in downtown Louisville

Kentucky / Louisville

Louisville house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$500

Price per night from

$500