Holiday rentals in Hills and Dales

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.

4.93 out of 5 average rating, 107 reviews

Villa in Prospect

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.

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.

Guest suite in Louisville

4.94 out of 5 average rating, 276 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.

5 out of 5 average rating, 209 reviews

Cabin in Louisville

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.

4.95 out of 5 average rating, 171 reviews

Home in Louisville

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 suite in Jeffersonville

4.96 out of 5 average rating, 131 reviews

Cozy! Minutes from Louisville. No cleaning fees.

NO CLEANING FEES!Relax in this modern yet cozy space. (2)Queen beds/bedrooms, (1)Queen air mattress available NOTE: We too reside in upper level but will not invade your privacy. NO SHARED LIVING SPACE. 6 minutes to 2nd St bridge/65S to downtown Louisville or 2 minutes to East End Bridge (265E) to Louisville LOU (SDF) Airport 20 min CHURCHILL DOWNS 21 min Highland Festival Grounds/Ky Expo Ctr 18 min LOU Waterfrnt 12 min KFC YUM Ctr 12 min Ky Kingdom 16 min

4.91 out of 5 average rating, 545 reviews

Guest house in Clifton

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 house 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.)

4.98 out of 5 average rating, 166 reviews

Dome in Mount Washington

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

Guest house in Jeffersonville

4.87 out of 5 average rating, 210 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!

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

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Popular amenities for Hills and Dales holiday rentals

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Other great holiday rentals in Hills and Dales

5 out of 5 average rating, 8 reviews

Home sweet home Newly built house with an electric vehicle charging outlet

CalvinRating, 5 stars5 days 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.

4.99 out of 5 average rating, 174 reviews

Flat in Crescent Hill

Urban Bourbon Farm Loft

RickRating, 5 stars2 weeks ago

This was our second stay and we had a very nice time. The inside is very clean and comfortable.

Guest suite in Windy Hills

4.95 out of 5 average rating, 55 reviews

Comfy Getaway Guest Suite in Louisville

AndreaRating, 5 stars3 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!

4.93 out of 5 average rating, 76 reviews

Beachfront River Cottage

TylerRating, 5 stars3 months ago

This was one of my favorite Air BNB stays to date. The cottage was so incredibly beautiful. It was super well stocked, clean, and there was a great amount of information about the property. We will definitely be back.

5 out of 5 average rating, 38 reviews

Flat in Jeffersonville

Private King Suite

KyriaRating, 5 stars5 days ago

Pamela’s place was exactly as described!! We had a great stay, and we definitely recommend for a little getaway! I loved how flexible check in/out time was. A good amount of amenities was provided as well. We couldn’t complain and I’d definitely book again.

5 out of 5 average rating, 23 reviews

Loft in Pewee Valley

The Valley Loft

JonathanRating, 5 stars4 weeks ago

Fantastic place. Nestled in the lush green countryside, 5 mins from an interstate you cannot hear, & 15 mins from the metro/downtown. Easy dedicated parking & patio, just to the side of owner's garage, park just feet from your stairs/door, with privacy fence. Very comfortable bed, useful desk & sitting area, well equipped kitchen, great lighting options, excellent HVAC mini-split, good wifi internet, & low radon levels. Best part is the windows & natural light.....especially the wonderful cross breeze ability, & more so the magnificent huge green trees to enjoy from the living room area or the desk area. Definitely try the free Merlin app for identifying birds. Wonderful rural roads for nice long walks or runs or biking in nature, & a few sidewalks/paths down Rollington to Central to the loop to the main street of Mt Mercy Dr. If up for an alternate walk/run/bike adventure, try the low-use Greenway path along the I-265 bridge over the Ohio River. And/or the Anchorage Trailhead.