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    Don't let other travellers get your favourite Charlestown area vacation rental. You're so close to securing your perfect getaway. Book today.
    39 Matching Rentals in the Charlestown AreaView all 77 rentals
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    Charlestown
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    The following rentals are within 25 kilometres of Charlestown.
    Large Historic Home, Walk to Dinner, parks, cafes!1 / 33
    (4)Excellent
    Louisville, KY
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Home away from Home1 / 56
    (2)Excellent
    Louisville, KY
    7 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    6 Bedroom Italianate Mansion in Historic Zone, Wall to All!1 / 27
    (10)Excellent
    Louisville, KY
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
    • Grill
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 23, 2019
    The owners are such wonderful people. . When you walk in you are transported to a wonderful old European home. The interior design is outstanding. Everywhere you look there is...
    Reviewed September 26, 2018
    We came in with a group for a local conference, and found that this house worked very well for our needs. The 6 of us had way more than enough space, and really enjoyed the open...
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    About this property
    Historic Mansion with all modern updates and a fabulous location! 6 bedroom, 5 bath house built in 1882 in a folk Italianate style with 12 foot ceilings, 10 foot tall windows, original crystal chandeliers and hardwood floors with 6000 square feet of living space. 5 miles from Churchill Downs...
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    Louisville, Kentucky 40204
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
    Derby City Digs1 / 16
    (3)Very good
    Louisville, KY
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
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    Reviewed May 29, 2018
    Recently rented the property for five nights and we could not have been more pleased! Rachelle and Jason were phenomenal and the house was just perfect. The pictures in the...
    Reviewed April 26, 2017
    Enjoyed our stay here . It is within 10 minute drive to expo center , Churchill Downs , and the downtown area.
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    About this property
    Cozy 2 bedroom apartment centrally located to all neighborhoods and attractions in Louisville. Convenient street parking in the front. The original shotgun house was built at the turn of the century with the camelback addition added in 1920. It has been renovated over the years to include...
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    Louisville, Kentucky 40217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Best Location!!! - Huge Historic Charm - 3BR-3BTH1 / 25
    (2)Excellent
    Louisville, KY
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    Reviewed July 10, 2018
    The location is close to downtown activities and walking distance to cool restaurants and bars in Butchertown. It is a charming older house which is totally updated. It worked...
    Reviewed September 19, 2017
    Great location right off the interstate. Close to downtown and tourist locations. Updated master bathroom and kitchen. Well decorated and squeaky clean.Easily accommodated six...
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    About this property
    Looking for that perfect house to experience one of the finest neighborhoods for dining, culture, arts, and shopping? Also looking for that fun historic home set up with thoughtfulness and flair? You must visit this charming home located next to historic Hadley Pottery and the 2nd oldest working...
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    Louisville, Kentucky 40206
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Middletown, KY
    8 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    About this property
    This spacious executive home, located 20 minutes to Churchill Downs! Beautiful home, sits on the 10th fairway of the Lake Forest Golf Course with views of the Country Club and Lake. 6 bedrooms, including 2 master suites, lower level kitchen, & walk-out. The pictures don't completely reflect...
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    Middletown, Kentucky 40245
    Holiday Rental House - 8 Bedrooms, 4 Bathrooms, Sleeps 16
    GERMANTOWN GEM CLOSE TO EVERYTHING DERBY!1 / 12
    (1)Excellent
    Louisville, KY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed November 5, 2018
    Excellent location. Great stay. Kendra had the home well stocked with beverages and more. Home has 2 king beds and some couches, we brought an air mattress. We would book...
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    About this property
    3 Bedroom, 1.5 Bathroom, Sleeps 6+ Located in beautiful germantown! Friendly neighborhood! Walking distance to local bars, pubs, brewery 8 MINUTES TO CHURCHILL DOWNS! Located minutes from downtown.......Nulu......Highlands.......Bardstown Road.......Ali Center......Churchill Downs.....Airport...
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    Louisville, Kentucky 40217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Louisville, KY
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
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    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is your perfect getaway luxurious rental for Derby weekend or any other long weekend or vacation! Welcome to our love nest that is conveniently located only 2.6 miles from Churchill Downs, 6 min from Downtown Louisville, 9 min from the airport and the famous Bardstown Rd with all its splendid...
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    Louisville, Kentucky 40217
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Country Living in the City-Open for the 2017 Derby1 / 22
    (2)Average
    Louisville, KY
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 17, 2017
    Beautiful, lush green forest right behind the backyard! My daughter loved talking to the squirrels that were always around. And birds we have never seen before constantly...
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    About this property
    Louisville, KY is a fabulous city with so much to offer everyone who visits the area for work or for pleasure enjoys Louisville. We now also have free ultra high speed Wifi. The Fair Grounds and Churchill Downs is 15 minutes away. With 'Lyft' driving/taxi service you can get to our home from the...
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    Louisville, Kentucky 40272
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sellersburg Ranch House1 / 44
    (1)Excellent
    Sellersburg
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1700 SqFt All Brick Ranch House in quiet Sellersburg suburb. Close to HWY 65, shopping places and 20 minutes from Downtown Louisville. This is perfect place to stay for transient travelers needing some rest and modern amenities, WiFi, Netflix, Garage parking. There’s coffee breakfast bar to get...
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    Sellersburg, Indiana 47172
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Louisville, KY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
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    About this property
    This unit is nestled in a lovely, quaint neighborhood of Louisville. The house is located a few steps from the public transportation line and is a 15 minute ride or drive to all major attractions in Louisville, including Churchill Downs, Convention Center, all downtown hotels, Fourth Street Live,...
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    Louisville, Kentucky 40241
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Louisville, KY
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our charming 100 yr old newly renovated home is located in the best part of Frankfort Ave area. Walk to top restaurants, shops, bars, cafes & farmers market! Features 2 BR (3 bed options, 2 futons), 2 baths, large family area, deck & excellent outdoor space. Pet Free. Location, Location, Location!...
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    Louisville, Kentucky 40206
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Louisville, KY
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Patio
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    • Porch
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great spacious, 3,000 SF house. 4 bedroom, 2.5 bath, finished basement with HD projection TV, Screed porch and patio. Conveniently located minutes from Churchill, airport and many restaurants. The Space *Located in the secluded Northfield neighborhood. *Walk to Starbucks or Heine Brothers Coffee...
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    Louisville, Kentucky 40222
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Saint Matthews, KY
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This beautiful, modern, quad-level home is centrally-located in quaint St. Matthews area which is minutes from both LOUISVILLE airports. Our goal for your stay is to make sure that your experience of Louisville/KY Derby/ChurchillDowns/Bourbon Trail is one that you will never forget. We look...
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    Saint Matthews, Kentucky 40207
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
    Louisville, KY
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • DVD Player
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely 4 bedroom 4 1/2 bath ranch home has all the amenities and proximity needed for a fabulous Kentucky Derby. Conveniently located off Newburg Road in the Heart of the HIghlands! You will be 4.1 miles to Churchill Downs, 2 miles from the Louisville International Airport and all of the...
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    Louisville, Kentucky 40205
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Louisville, KY
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This stunning home has just undergone a complete remodel. Lovely original details were kept and every modern luxury added. Over 3700 square feet of living space with an attached garage and additional off street parking for up to 4 cars. The home has five bedrooms and five bathrooms with bedding...
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    Louisville, Kentucky 40204
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Louisville, KY
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Sauna
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Visit our Facebook page for more pics and info. Just search for Sunset Manor. The perfect mix of privacy, luxury, and fun. The house sets on 8 acres on Floyd's Fork. There are beautiful views of the creek and hills from the wrap around front porch. Inside enjoy all the amenities of the over 5000...
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    Louisville, Kentucky 40245
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Close To Downtown In Historic Crecent Hill1 / 13
    (1)Excellent
    Louisville, KY
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2017
    The location of this house is fantastic. It's minutes away from downtown, and within walking distance of fantastic shops and food. The owner was very gracious and took...
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    About this property
    Large, well maintained home in a quiet neighborhood minutes from interstates 71, 64 and 65 and downtown. Within walking distance of Frankfort Ave, home to some of the best restaurants in town, wonderful little boutiques, antique stores, and high end resale shops. 5 star experience complete. Plenty...
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    Louisville, Kentucky 40206
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Henryville
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Stone Creek, a private 3 acre estate conveniently located minutes to Louisville, KY. This is the Ultimate Getaway! Upon entering the premises, you will find a custom iron security gate requiring coded access. Stone Creek boasts 2500+ sq ft of luxury living space complete with a full...
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    Henryville, Indiana 47126
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Louisville, KY
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This home was built in 1910 and located in the historic Highlands area. It is a duplex with a second and third floor approximately 2400 sqft. It is walking distance to over 30 bars, restaurants, liquor stores, activities and Cherokee Park with lots of walking and biking trails. Daniel Boone statue...
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    Louisville, Kentucky 40205
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Louisville, KY
    4 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    About this property
    Location! Location! Location! Welcome to the Derby City House. While staying here, you will be steps away from Churchill Downs (.5 miles), Kentucky Fair and Expo Center (1.4 miles), Jim Patterson Baseball Field (.4 miles), Papa Johns Cardinal Stadium (1.1 miles), 4th St Live (5.6 miles), and a 5...
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    Louisville, Kentucky 40214
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 9
    Louisville, KY
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
    About this property
    Only 8 minutes from Churchill downs and 6 minutes to UofL! You will love our newly remodeled, decorated, clean and fresh corner gem with plenty of yard space for your next family or social gathering among friends. Guests are able to use all the space in the living area downstairs which includes...
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    Louisville, Kentucky 40217
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Prospect, KY
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 6,500 Sq ft home is built for comfort AND convenience. Located off of the GeneSnyder Freeway and 5 minutes from the Watterson XWay, Churchill Downs is a 20 minute drive with popular restaurants and shopping nearby. LOTS OF ROOM TO PRIMP THE OAKS/DERBY EXPERIENCE is all about the beautiful...
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    Prospect, Kentucky 40241
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Louisville, KY
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    Located right off Bardstown Road and the Watterson Expressway. Quick and easy access to get to Churchill Downs or the best bars/restaurants in the eclectic highlands neighborhood on Bardstown Road. There is a fenced backyard, 2 car garage and basement. Recently remodeled bathroom and living room....
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    Louisville, Kentucky 40220
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Louisville, KY
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Victorian duplex home with the bottom portion available for stays. The perfect place to tour Louisville with the house close to all the dining, experience, and nightlife imaginable. There is an outdoor area with a picnic table for having a wonderful meal outdoors. Oh, and before you visit, it is...
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    Louisville, Kentucky 40204
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Louisville, KY
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    About this property
    Awesome for Derby and preceding events. Great location. 7 couples can share the house. Once in a lifetime experience. Late cancellation made it available. Will go fast. Pictures available. Just deep cleaned. Comfortable beds. On 5 acre lot. Six nights gives you the parade, boat race and oaks Friday...
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    Louisville, Kentucky 40245
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    Louisville, KY
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
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    About this property
    Our charming two story colonial is located in the historic Highlands district. We are walking distance to two scenic parks as well as many stores and restaurants. Churchill Downs is an easy 15 minute drive. We have three bedrooms, two and a half baths. Our living room has a spacious sectional plus...
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    Louisville, Kentucky 40205
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    New Albany
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    BRAND NEW LISTING! Spacious and bright, this newly remodeled 2br and 2ba contemporary-modern home in historic New Albany is perfect for you and your family. You will be delighted with the accessibility and quick travel to downtown Louisville, KY or other cities in Southern Indiana. Ten minutes to...
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    New Albany, Indiana 47150
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Louisville, KY
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    This brand new listing is a chic & tastefully designed 4 br 2 ba home in the heart of Louisville's Germantown district. It can accommodate up to 10 guests and is located close to EVERYTHING. Just minutes from the best bars and restaurants in the city. Whether you’re headed downtown, the track or...
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    Louisville, Kentucky 40204
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Louisville, KY
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This house is located in the center of the town and close to many attractions including Bardstown, Churchill Downs, Downtown, Kentucky Expo, Kentucky Kingdom, UofL. Many dining options are in the walking distance. 2 popular bus routes are 1-minute walking. Nice for business trips and short...
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    Louisville, Kentucky 40217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Louisville, KY
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Our 4 BR 2.5 bath 110 yr old home has 2400 square feet & is just 3.5 BLOCKS from Bardstown Road, the main restaurant/bar district. Coffee shops, book stores, the city's hippest restaurants and bars, Cherokee Park...all the amenities you could want within walking distance! We can provide air...
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    Louisville, Kentucky 40204
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Jeffersonville
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to Arctic Springs, a lovely street along the Ohio River just upriver from downtown Jeffersonville, Indiana and Louisville, Kentucky. Originally camps on the river, most of the homes have been expanded or rebuilt over the years. Ours had a second floor added, which is what you will use while...
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    Jeffersonville, Indiana 47130
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Home rental
    Louisville, KY
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Thank you for clicking! Our home is centrally located in Louisville, Kentucky and is available for rent for the entire exciting week of The Kentucky Derby. We are locatec a short drive to Churchill Downs. Please contact us via email with any questions about our home or the location. Thank you for...
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    Location Information
    Louisville, Kentucky 40205
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Louisville, KY
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Parking
    • Air Conditioning
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay in downtown Louisville home for the KY Derby! It's only 3.5 miles from Churchill Downs Racetrack and is an easy walk to 4th St. Live! There is one king bed, one queen bed, one full bed, two queen air mattresses, and two couches that can be used for sleeping. At least 2 nights are...
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    Location Information
    Louisville, Kentucky 40202
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Prospect, KY
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Terrace
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2,600-square-foot riverfront home features 3 well-appointed bedrooms and 2.5 baths for a memorable stay in Louisville! Situated in the upscale and peaceful Prospect neighborhood, this home is only 15 miles to the excitement of downtown. Kick back on the furnished deck to wind down as you...
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    Location Information
    Prospect, Kentucky 40059
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Pewee Valley, KY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to Louisville and stay at this house in the East End! Situated in a quiet neighborhood yet just minutes to several freeways, this is the ultimate home base for experiencing everything the 'Gateway to the South' offers. Along with an ideal location, only 25 minutes from Churchill Downs and...
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    Location Information
    Pewee Valley, Kentucky 40245
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Louisville, KY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Washer
    • Patio
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in the early 1900s and outfitted with contemporary comfort for 4 guests, this hip 2-bedroom, 2-bathroom house is set in the heart of the Highlands neighborhood of Louisville. 'The Derby House on the Hill' is well appointed with an open backyard - just steps away from Bardstown Road - where...
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    Location Information
    Louisville, Kentucky 40204
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    New Albany
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether you’re visiting for the Kentucky Derby, to taste your way along the Bourbon Trail, or to hang out at Fourth Street Live, this vacation rental is the ultimate home base! Located in New Albany, just across the river from downtown Louisville, this 3-bedroom, 2-bath house is ideal for groups of...
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    Location Information
    New Albany, Indiana 47150
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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