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
A spacious living area features a modern kitchen with high-end appliances and a breakfast bar. Dark-stained wooden beams contrast with the light-colored walls, while hardwood floors add warmth. A cozy gray armchair and decorative tables complete the inviting space, complemented by a wall-mounted TV.
Apartment in Cherokee Triangle
4.94 out of 5 average rating, 317 reviews

Chic, Luxurious Carriage House in Ideal Location

Selected by Architectural Digest as best Airbnb in Kentucky. Sink into the rounded, studded armchair under exposed wooden beams at a characterful retreat with minimal, modern style. This historic space contrasts deluxe touches including the 6-foot soaking tub with sash windows and a sliding barn door. This fully furnished apartment is perfect for a getaway weekend or for short to medium rental as an executive apartment. The historic property has been lovingly renovated as a luxurious apartment with high-end finishes while maintaining the historic character of its past as a carriage house. You enter the apartment through a hallway that houses a dedicated washer and dryer. Upstairs features a large living/working space, a beautiful kitchen with brand new-high end appliances, and a 50" 4K smart TV. The sliding barn door separates the bedroom, where you will also find a large walk-in closet, a marble bathroom with a 6 foot soaking tub, and a brand new queen sized Tuft and Needle mattress. We will meet our guests and orient them to the house and neighborhood, or provide self check-in depending on preference. For the remainder of your stay, we will be close by for any additional needs. Cherokee Triangle is one of the most historic neighborhoods in Louisville, built in the late 19th century and part of the larger Highlands area. The tree-lined streets are a short walk from the restaurants, bars, and boutiques on Bardstown Road. You do not need a car around here - everything is a short walk away. Parks, restaurants, shops, grocery stores are all within 5 minutes on foot. Downtown or Churchill Downs are is a 5-10 minute drive away. Street parking is available.

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 cozy outdoor firepit area is surrounded by Adirondack chairs, arranged in a circle on a gravel surface. Soft, warm lights hang overhead, illuminating the space against a serene, wooded backdrop, creating an inviting atmosphere for gatherings.
Villa in Prospect
4.93 out of 5 average rating, 133 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.

Top Guest favourite
Condo in Saint Matthews
4.96 out of 5 average rating, 272 reviews

The Sweet Spot! - Live Like a Local

Live like a local in one of Louisville’s most sought-after neighborhoods, young professionals and families alike. Rich in history and surrounded by wall-to-wall dining, shopping, and entertainment, this vibrant area is known for its charm, energy, and premium appeal. Originally built as a single condo over two decades ago, the owner later acquired the neighboring unit and completely reimagined the entire second level. The result is a thoughtfully crafted space that truly feels like a retreat.

Top Guest favourite
A charming house is framed by lush greenery, with a well-maintained yard featuring a white fence. An inviting driveway leads to the entrance, while American flags adorn the porch. The surrounding trees provide a serene, wooded backdrop.
Guest suite in Louisville
4.94 out of 5 average rating, 307 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 a charming single-story house is shown, featuring a covered porch and stone columns. Lush green bushes frame the entrance, and two seats are visible on the porch. A modest yard surrounds the house, with a clear sky above.
Home in Clifton Heights
4.91 out of 5 average rating, 310 reviews

Quiet Neighborhood Home With Outstanding Location

Situated on a quiet hilltop neighborhood in Clifton Heights, this is the perfect location for a professional or personal visit to Louisville and very animal friendly. It is within 10 minutes of Downtown, Waterfront Park, Nulu, Frankfort Avenue, the Highlands, the Convention Center, and just 15 minutes from historic Churchill Downs. These neighborhoods feature the best dining and entertainment in the city. Just a block away is the Mellwood Arts Center complex with shops and dining.

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, 225 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, 253 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.

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, 223 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.

Guest favourite
Home in Jeffersonville
4.92 out of 5 average rating, 175 reviews

Scandinavian Retreat: Cozy Stay near Louisville

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 cozy home boasts 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 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, 174 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.

Top Guest favourite
A blue carriage house is viewed from the driveway, surrounded by greenery and blooming trees. Steps lead to an upper balcony, offering outdoor potential. The driveway provides easy access to the garage, emphasizing a sense of space and privacy.
Guesthouse in Louisville
4.92 out of 5 average rating, 1,138 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.

Popular amenities for Hills and Dales holiday rentals