Vacation rentals in Hills and Dales

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Top-rated vacation rentals in Hills and Dales

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Top guest favorite

Guest suite in Jeffersonville

4.94 out of 5 average rating, 205 reviews

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Guest favorite

Apartment in Jeffersonville

4.97 out of 5 average rating, 130 reviews

Cozy Riverside Stay – King Bed, Mins to Downtown!

Enjoy a peaceful stay at this Cozy apartment right off of the river in Jeffersonville, minutes from the heart of Downtown Louisville! With stylish decor, a fully stocked kitchen, and a comfortable king size memory foam mattress great for a good night's sleep, you'll be living lavishly during your stay! Enjoy a peaceful evening walk over the bigfour bridge and get a view of the beautiful city skyline, or stay in for a movie night with the multitude of streaming services! Book your stay today!

Guest favorite

Villa in Prospect

4.94 out of 5 average rating, 108 reviews

Bourbon Trail, Firepit

After a beautiful drive along a tree-lined-canopied road, you will find Mint Julep Villa, located on a private 1.3 acre lot and just one street over from the Ohio River. Mint Julep Villa, is tastefully decorated for you and your family to enjoy your stay in the Louisville and Prospect KY area. No matter if it's the Bourbon trails, the Kentucky Derby, the numerous concerts and the many other attractions to draw you to Kentucky, Mint Julep Villa will be a place you'd be attracted to as well.

Top guest favorite

Home in Jeffersonville

4.96 out of 5 average rating, 103 reviews

The Cloud - New Luxury Home With EV Charger

New 3 bed / 3 Bath, 2 King beds and 1 Queen. Spacious garage with EV charger, furnished patio with grill. Located in the heart of Jeffersonville's expansion and about 18 miles from Louisville International Airport and 7 Mi to Dtwn Louisville. Short distance to highways, shopping centers. Walking access to Vissing Park trails. Open floor plan with 10' ceiling, 65" smart TV and 50" smart TV in each bedroom. Kitchen fully equipped. Treadmill, 1 high chair and 1 portable pack and play for babies.

Top guest favorite

Guest suite in Louisville

4.94 out of 5 average rating, 277 reviews

Hide away close to everything

Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

Top guest favorite

Cabin in Louisville

5 out of 5 average rating, 212 reviews

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Top guest favorite

Home in Louisville

4.95 out of 5 average rating, 171 reviews

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

Guest favorite

Guesthouse in Clifton

4.91 out of 5 average rating, 546 reviews

Cute Carriage House off Frankfort Avenue

Welcome to "The Cute Carriage House at Frankfort Avenue". Experience serenity in a genuine "tiny house” that comfortably accommodates two people. There are several sleeping options that I will mention below. We are located a short block from premier restaurants and shops on Frankfort Avenue in the classy Clifton Neighborhood...and close to Cherokee Park and the cool Bardstown Road. FYI https://www.leoweekly.com/2020/10/the-winners-of-the-2020-readers-choice-awards/

Guest favorite

Guesthouse in Louisville

4.97 out of 5 average rating, 131 reviews

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

Guest favorite

Guesthouse in Jeffersonville

4.87 out of 5 average rating, 211 reviews

The Cottage Next Door

Looking for a cozy, clean place to rest your head while you explore? Comfort, simplicity and value- perfect for travelers who care more about adventure than luxury. We offer quiet, efficient and sparkling clean- everything you need to recharge after a day of soaking in the local sights, bites and vibes. We keep our prices low because we believe travel should be about the experience, not the expense. Book now and start your next adventure!

Guest favorite

Home in Jeffersonville

4.95 out of 5 average rating, 135 reviews

Scandinavian Retreat: <20 mins to Churchill Downs

Come stay in this cozy 3 bedroom, 1.5 bathroom townhouse, designed to make you feel at home while visiting Southern Indiana or Louisville, Kentucky. A few minutes to downtown night life, museums, Louisville, UofL, and close to bourbon trail this brand new home boasts new memory foam beds, furniture, full kitchen & more. Fast WiFi (~300mbs) 50" smart HDTV Parking for 2 cars 13 minutes to the YUM! Center

Top guest favorite

Guesthouse in Louisville

4.93 out of 5 average rating, 1,010 reviews

HIghlands Modern Get Away

Ideal, quiet place in the highlands. You have the apartment over the garage. You'll have a place all to yourself with most the amenities of your own home. Studio apartment with a balcony if you decide to hang out and relax for the evening. There is a cook top, but no oven in the kitchen. Park in the driveway in front of the garage. Pets are welcome, plz add them when booking.

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Other great vacation rentals in Hills and Dales

Guest favorite

Private room in Jeffersonville

4.92 out of 5 average rating, 706 reviews

Zen Room minutes from downtown!

RyanneRating, 5 stars2 weeks ago

Great stay…Tamyra was so accommodating and responsive. The room we stayed in and the overall house are all so cozy and peaceful and the back yard is lovely.

Home in Shelby Park

5 out of 5 average rating, 4 reviews

Colonel Lou Lou's

WillRating, 5 stars3 days ago

Had a wonderful time here and would love to come back. Had wonderful recommendations and felt right at home.

Top guest favorite

Home in Jeffersonville

5 out of 5 average rating, 8 reviews

Home sweet home 新建房的房源，带电动车充电插座

CalvinRating, 5 stars1 week ago

Wonderful home and location and the amenities at the home went above and beyond our expectations. Highly recommend booking with Rita as everything went smoothly and she was very responsive.

Top guest favorite

Apartment in Crescent Hill

4.99 out of 5 average rating, 177 reviews

Urban Bourbon Farm Loft

MatthewRating, 5 stars3 days ago

It was a great place, has everything you need!

Guest favorite

Condo in Saint Matthews

4.9 out of 5 average rating, 30 reviews

Chateau St. Matthews: Style & Quiet 1B Condo

TiffanyRating, 5 stars1 month ago

We had a wonderful stay at Patrice's place! The apartment was incredibly clean and well-equipped and the location was close enough for exploring the city. Patrice was also extremely responsive and helpful, always going above and beyond to ensure our comfort and offering assistance in any way. I highly recommend! Pleasant experience. The location of the condo was near to many of the places we wanted to visit. It was about a 10 min Uber ride to the Downtown District during Kentucky Derby weekend. It was about a 15 to 20 min ride to Churchill Downs.

Guest favorite

Guest suite in Windy Hills

4.95 out of 5 average rating, 55 reviews

Comfy Getaway Guest Suite in Louisville

AndreaRating, 5 stars4 weeks ago

Keith and Angela’s place was the perfect place to stay while visiting my parents in Louisville. We were walking distance from my parents and really enjoyed being close to the restaurants in Holiday Manor. The hosts were super responsive when we had questions about parking and controlling the AC when we got a little chilly. The apartment was spacious and comfortable and we can’t wait to stay there again the next time we’re in town!

Guesthouse in Louisville

4.85 out of 5 average rating, 26 reviews

Chic Louisville Carriage Apt - Game Room -Sleeps 4

TonyRating, 5 stars1 month ago

This was the place I needed for the weekend. It was very Peaceful and the place was so nice, clean and relaxing! Maria was so nice and very easy to communicate with. I would recommend this place to everyone.

Guest favorite