Charlestown Rentals

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93 Houses

    24

    ‘Governor’s Mansion’ - Louisville Home w/Hot Tub!

    Indiana / Charlestown

    Charlestown house

    6 12 min stay varies

    • 6 bedrooms
    • sleeps 12
    • min stay varies
    • Child Friendly
    • Air conditioning

    Price per night from

    $457

    Responds fast!
    avg. 1 hour 33 minutes

    Price per night from

    $457

      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

      $157

      Responds fast!
      avg. 3 hours 58 minutes

      Price per night from

      $157

        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

        $109

        Responds fast!
        avg. 29 minutes

        Price per night from

        $109

        Great rentals within 20 miles that match your search

        Distance approx 16.22 km from Charlestown

        (3) Very Good 

          16

          Derby City Digs

          Kentucky / Louisville

          Louisville house

          2 6 2 nights min

          • 2 bedrooms
          • sleeps 6
          • 2 nights min
          • Child Friendly

          Price per night from

          $102

          Responds fast!
          avg. 1 hour 24 minutes

          Price per night from

          $102

          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

            $155

            Responds fast!
            avg. 47 minutes

            Price per night from

            $155

            Distance approx 14.52 km from Charlestown

            (9) Excellent 

              15

              2 bed/2.5 bath Historic District Luxury Townhouse

              Kentucky / Louisville

              Louisville apartment

              2 7 min stay varies

              • 2 bedrooms
              • sleeps 7
              • min stay varies
              • Child Friendly
              • Car not necessary
              • Air conditioning
              “Super location - highly recommend” Stayed with spouse and two teenaged children while visiting family. The condo was located in an area with a lot of restaurants within walking distance that worked for both groups. It was well stocked and really com
              …see more

              Price per night from

              $212

              Responds fast!
              avg. 2 hours 56 minutes

              Price per night from

              $212

              Distance approx 14.51 km from Charlestown

              (1) Excellent 

                5

                Carriage House, First Floor

                Kentucky / Louisville

                Louisville house

                2 5 min stay varies

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

                Price per night from

                $95

                Price per night from

                $95

                Distance approx 18.22 km from Charlestown

                  20

                  Exquisite executive retreat!

                  Kentucky / Eastwood

                  Eastwood villa

                  5 10 7 nights min

                  • 5 bedrooms
                  • sleeps 10
                  • 7 nights min
                  • Child Friendly
                  • Pet Friendly

                  Price per night from

                  $1,309

                  Price per night from

                  $1,309

                  Distance approx 14.81 km from Charlestown

                  (4) Very Good 

                    32

                    Comfortable 3bed/2bath Home - Highlands, Louisville

                    Kentucky / Louisville

                    Louisville house

                    3 6 3 nights min

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

                    Price per night from

                    $138

                    Responds fast!
                    avg. 3 hours 15 minutes

                    Price per night from

                    $138

                    Distance approx 14.47 km from Charlestown

                    (4) Excellent 

                    Certificate of Excellence

                      33

                      Large Historic Home, Walk to Dinner, parks, cafes!

                      Kentucky / Louisville

                      Louisville house

                      6 16 min stay varies

                      • 6 bedrooms
                      • sleeps 16
                      • min stay varies
                      • Child Friendly
                      • Car not necessary
                      • Air conditioning

                      Certificate of Excellence

                      Price per night from

                      $361

                      Responds fast!
                      avg. 2 hours 56 minutes

                      Price per night from

                      $361

                      Distance approx 14.04 km from Charlestown

                        36

                        Private In-Law Suite, Business Travel

                        Kentucky / Anchorage

                        Anchorage house

                        1 2 2 nights min

                        • 1 bedroom
                        • sleeps 2
                        • 2 nights min
                        • Swimming pool
                        • Air conditioning
                        • Private garden

                        Price per night from

                        $85

                        Price per night from

                        $85

                        Distance approx 9.47 km from Charlestown

                        (1) Excellent 

                          18

                          Kentucky suite with the comforts of home.

                          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

                          $126

                          Price per night from

                          $126

                          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

                            $172

                            Responds fast!
                            avg. 8 minutes

                            Price per night from

                            $172

                            Distance approx 11 km from Charlestown

                              19

                              Kentucky Derby Rental - Close in, East End

                              Kentucky / Louisville

                              Louisville house

                              4 8 3 nights min

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

                              Price per night from

                              $2,863

                              Price per night from

                              $2,863

                              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

                                $403

                                Price per night from

                                $403

                                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

                                  $2,182

                                  Price per night from

                                  $2,182

                                  Distance approx 14.54 km from Charlestown

                                    11

                                    Great location on Cherokee Road -Second Floor

                                    Kentucky / Louisville

                                    Louisville apartment

                                    1 2 min stay varies

                                    • 1 bedroom
                                    • sleeps 2
                                    • min stay varies
                                    • Swimming pool
                                    • Child Friendly
                                    • Car not necessary

                                    Price per night from

                                    $78

                                    Price per night from

                                    $78

                                    Distance approx 13.34 km from Charlestown

                                      25

                                      Cozy St. Matthews Home w/ Deck & Prime Walkability!

                                      Kentucky / Saint Matthews

                                      Saint Matthews house

                                      2 6 min stay varies

                                      • 2 bedrooms
                                      • sleeps 6
                                      • min stay varies
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $126

                                      Responds fast!
                                      avg. 8 minutes

                                      Price per night from

                                      $126

                                      Distance approx 13.53 km from Charlestown

                                        23

                                        Charming shotgun in walkable district | Louisville

                                        Kentucky / Louisville

                                        Louisville house

                                        2 4 2 nights min

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

                                        Price per night from

                                        $287

                                        Responds fast!
                                        avg. 8 minutes

                                        Price per night from

                                        $287

                                        Distance approx 14.42 km from Charlestown

                                        (9) Excellent 

                                        Certificate of Excellence

                                          27

                                          6 Bedroom Italianate Mansion in Historic Zone, Wall to All!

                                          Kentucky / Louisville

                                          Louisville house

                                          6 16 min stay varies

                                          • 6 bedrooms
                                          • sleeps 16
                                          • min stay varies
                                          • Ask about children
                                          • Car not necessary
                                          • Air conditioning
                                          “Great House!” We stayed for Ford Iron Man for 5 nights. 7 adults, 2 teens, 1 child. Stunning home- not your average rental house, but a huge, stately place that still has everything from plasma TVs to wifi. We arrived a little early to find the home
                                          …see more

                                          Certificate of Excellence

                                          Price per night from

                                          $825

                                          Responds fast!
                                          avg. 2 hours 56 minutes

                                          Price per night from

                                          $825

                                          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

                                            $2,863

                                            Price per night from

                                            $2,863

                                            Distance approx 15.25 km from Charlestown

                                              24

                                              NEW! Cozy Louisville Home w/Yard in Shelby Park!

                                              Kentucky / Louisville

                                              Louisville house

                                              2 6 min stay varies

                                              • 2 bedrooms
                                              • sleeps 6
                                              • min stay varies
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $103

                                              Responds fast!
                                              avg. 9 minutes

                                              Price per night from

                                              $103

                                              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

                                                $401

                                                Responds fast!
                                                avg. 7 minutes

                                                Price per night from

                                                $401

                                                Distance approx 9.06 km from Charlestown

                                                  14

                                                  Beautiful KY Derby Home/15 miles from track

                                                  Kentucky / Prospect

                                                  Prospect house

                                                  4 8 3 nights min

                                                  • 4 bedrooms
                                                  • sleeps 8
                                                  • 3 nights min
                                                  • Air conditioning
                                                  • Private garden

                                                  Price per night from

                                                  $2,863

                                                  Price per night from

                                                  $2,863

                                                  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

                                                    $567

                                                    Price per night from

                                                    $567

                                                    Distance approx 15.55 km from Charlestown

                                                      7

                                                      Old Louisville---Where It All Began

                                                      Kentucky / Louisville

                                                      Louisville apartment

                                                      1 2 1 night min

                                                      • 1 bedroom
                                                      • sleeps 2
                                                      • 1 night min
                                                      • Air conditioning

                                                      Price per night from

                                                      $58

                                                      Price per night from

                                                      $58

                                                      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

                                                        $68

                                                        Price per night from

                                                        $68

                                                        Distance approx 13.64 km from Charlestown

                                                          13

                                                          City Plex Studio #3, (grd fl. rear) New Albany IN

                                                          Indiana / New Albany

                                                          New Albany apartment

                                                          1 2 1 night min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 1 night min
                                                          • Nearest beach 730 mi
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $63

                                                          Price per night from

                                                          $63

                                                          Distance approx 14.51 km from Charlestown

                                                            10

                                                            Tree House Apartment

                                                            Kentucky / Louisville

                                                            Louisville apartment

                                                            1 4 min stay varies

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

                                                            Price per night from

                                                            $258

                                                            Price per night from

                                                            $258

                                                            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

                                                              $916

                                                              Price per night from

                                                              $916

                                                              Distance approx 14.68 km from Charlestown

                                                                26

                                                                FULLY RENOVATED 2br/2ba; 10min to Louisville. LOVELY new furnishings. QUIET!

                                                                Indiana / New Albany

                                                                New Albany house

                                                                2 8 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 8
                                                                • min stay varies
                                                                • Child Friendly
                                                                • Air conditioning
                                                                • Private garden

                                                                Price per night from

                                                                $171

                                                                Price per night from

                                                                $171

                                                                Distance approx 17.74 km from Charlestown

                                                                  28

                                                                  FANTASTIC HOME!!!☆DERBY CITY HOUSE☆

                                                                  Kentucky / Louisville

                                                                  Louisville house

                                                                  4 9 min stay varies

                                                                  • 4 bedrooms
                                                                  • sleeps 9
                                                                  • min stay varies
                                                                  • Child Friendly
                                                                  • Car not necessary

                                                                  Price per night from

                                                                  $172

                                                                  Price per night from

                                                                  $172

                                                                  Distance approx 15.14 km from Charlestown

                                                                    15

                                                                    The Orange Door - Derby Perfect Sleeps 10

                                                                    Kentucky / Louisville

                                                                    Louisville house

                                                                    4 10 2 nights min

                                                                    • 4 bedrooms
                                                                    • sleeps 10
                                                                    • 2 nights min
                                                                    • Child Friendly
                                                                    • Air conditioning
                                                                    • Private garden

                                                                    Price per night from

                                                                    $343

                                                                    Price per night from

                                                                    $343

                                                                    Distance approx 13.18 km from Charlestown

                                                                      12

                                                                      Luxury Loft in Historci Butchertown

                                                                      Kentucky / Louisville

                                                                      Louisville apartment

                                                                      2 8 2 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 8
                                                                      • 2 nights min
                                                                      • Child Friendly
                                                                      • Car not necessary
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $430

                                                                      Price per night from

                                                                      $430

                                                                      Distance approx 14.58 km from Charlestown

                                                                        16

                                                                        Turnkey Furnished 1 BR in Desirable Highlands with Pool and off-steet parking

                                                                        Kentucky / Louisville

                                                                        Louisville condo

                                                                        1 2 90 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 90 nights min
                                                                        • Swimming pool
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $132

                                                                        Responds fast!
                                                                        avg. 3 hours 0 minutes

                                                                        Price per night from

                                                                        $132

                                                                        Distance approx 16.1 km from Charlestown

                                                                          4

                                                                          Kentucky Derby Rental (Main Front)

                                                                          Kentucky / Louisville

                                                                          Louisville b and b

                                                                          1 2 3 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • 3 nights min

                                                                          Price per night from

                                                                          $2,004

                                                                          Price per night from

                                                                          $2,004

                                                                          Distance approx 13.43 km from Charlestown

                                                                          (3) Excellent 

                                                                            46

                                                                            Luxurious Frankfort Ave CoachHouse Stay/Event 6BD

                                                                            Kentucky / Louisville

                                                                            Louisville house

                                                                            3 16 min stay varies

                                                                            • 3 bedrooms
                                                                            • sleeps 16
                                                                            • min stay varies
                                                                            • Child Friendly
                                                                            • Car not necessary
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $567

                                                                            Price per night from

                                                                            $567

                                                                            Distance approx 13.94 km from Charlestown

                                                                              18

                                                                              Downtown Loft

                                                                              Kentucky / Louisville

                                                                              Louisville condo

                                                                              2 3 1 night min

                                                                              • 2 bedrooms
                                                                              • sleeps 3
                                                                              • 1 night min
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $261

                                                                              Price per night from

                                                                              $261