Holiday houses in Hills and Dales

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Top-rated holiday rentals in Hills and Dales

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Top Guest favourite
An outdoor fire pit is surrounded by several wooden chairs, providing a gathering space for relaxation. The calm waters of the Ohio River reflect the night sky, with soft lights from boats creating a serene atmosphere. Low greenery and gentle clouds frame the scene.
Guest suite in Jeffersonville
4.95 out of 5 average rating, 237 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.

Top Guest favourite
A welcoming exterior view of a stylish house features a covered front porch with seating and decorative elements. The spacious interior showcases a cozy living area with comfortable seating and art on the walls. A well-maintained outdoor space includes a putting green. Natural light brightens the rooms.
Home in Jeffersonville
4.99 out of 5 average rating, 110 reviews

Walking Bridge, Putt Putt House

NEW LISTING: Welcome to our walking bridge home on Pearl St. We have a hot tub, putt putt, and all the fun you can think of in one home. Steps away from restaurants, shopping, and bars, as well as the walking bridge to Louisville. This home is closer to the fun in Louisville than most neighborhoods in Louisville itself. Go out or stay in, you're guaranteed to have a great time in this newly renovated gem. We have high quality mattresses, and smart TV's in both bedrooms and the living room.

Top Guest favourite
Villa in Prospect
4.93 out of 5 average rating, 125 reviews

Bourbon Trail Firepit Hot Tub River Road Picnic

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 trail, 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.

Guest favourite
A charming log cabin is framed by lush green trees, showcasing a warm exterior with a stone chimney. Rocking chairs are placed on the front porch, surrounded by vibrant flowers and a neatly maintained garden path leading to the entrance.
Cabin in Louisville
4.95 out of 5 average rating, 352 reviews

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

Top Guest favourite
A colorful living area is furnished with a patterned sectional sofa and a round glass coffee table. Natural light enters through multiple windows, illuminating the artful wall decor. A kitchenette area with modern appliances is visible in the background, enhancing the space's functionality.
Guest suite in Louisville
4.94 out of 5 average rating, 301 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.

Guest favourite
The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.
Cabin in Louisville
4.98 out of 5 average rating, 256 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.

Guest favourite
A cozy living room is presented with a dark sofa facing a white-brick fireplace. Above the fireplace, a flat-screen television is mounted. Two armchairs flank the fireplace, while a small ottoman completes the seating arrangement. Light-colored drapes frame the windows, and artwork decorates the walls.
Home in Louisville
4.87 out of 5 average rating, 221 reviews

Private EAST END gem, minutes to everything!

Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

Top Guest favourite
A patio area features several blue chairs positioned on a textured surface, with a stone bench visible nearby. Lush green trees surround the space, providing a natural backdrop. In the distance, a red structure can be seen, framed by the greenery.
Guest suite in Prospect
4.97 out of 5 average rating, 250 reviews

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

Guest favourite
The bedroom features a spacious king-sized bed, adorned with decorative pillows, and a stylish ceiling fan above. A wooden chest sits at the foot of the bed, complemented by a desk and chair in the corner. Natural light enters through window treatments, illuminating the room.
Guesthouse in Louisville
4.96 out of 5 average rating, 137 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.)

Top Guest favourite
The inviting bedroom features a spacious bed with white linens and a soft green throw. A mounted projector is positioned on the ceiling, with greenery-patterned wallpaper creating a serene ambiance. Two bedside tables with lamps and a bench at the foot of the bed enhance functionality.
Guest suite in Louisville
4.99 out of 5 average rating, 217 reviews

Olive Branch Suite with projector screen in E Lou

This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.

Top Guest favourite
The exterior of a renovated farmhouse is surrounded by lush greenery. A spacious porch with seating is visible at the front, while a gravel path leads to the inviting entrance. The structure features a metal roof and warm-colored trim that complements the natural setting.
Farm stay in Goshen
4.98 out of 5 average rating, 354 reviews

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

Top Guest favourite
A cozy efficiency room features a spacious bed covered in patterned bedding and a comfortable couch. A mirror and decorative artwork adorn the walls, with bedside tables and soft lighting from lamps. The en-suite bathroom is partially visible in the background.
Guest suite in Louisville
4.96 out of 5 average rating, 170 reviews

One Room Apartment with Private Off Street Parking

Room is a stand alone efficiency with a kitchenette, blackout curtains, and reclining queen bed. It has one designated parking space and seperate entrance. Unit has private bath and walk in closet, and kitchenete. Also has refeigerator, coffee maker, work desk microwave, 42" smart tv, Ninja airfryer oven, and couch. Private porch with table and chairs. Close/secure single parking space.

Popular amenities for Hills and Dales holiday rentals