Holiday rentals in Windy Hills

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Top-rated holiday rentals in Windy Hills

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Guest favourite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 159 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 favourite

Guest suite in Louisville

4.97 out of 5 average rating, 110 reviews

Action City! Extravaganza at Bardstown Rd!

In the HEART of the Highlands, this spot sits near the corner of the main strip- just steps to Bardstown Rd. A few minutes drive to anywhere in city limits! And exactly where YOU want to be! Action Packed: Restaurants, Shopping, Bars, Parks, and Church- all walkable. A surprise local GIFT CARD given with each stay! This place is stylish, chic, cozy, and extremely quiet, as double pane windows have been installed. Recently renovated, it houses all the essentials for a weekend or week long stay.

Guest favourite

Townhouse in Louisville

4.95 out of 5 average rating, 219 reviews

Louisville Charm: Walk to it All! Central & Quaint

Welcome to the charm and character of Louisville! WALKING DISTANCE to everything you can enjoy. You will be right off the main strip of Frankfort Ave near Nulu. Less than a 5min walk to local breweries, coffee shops, restaurants, bars +more! Your experience includes: -queen suite -clawfoot tub shower combo -rollaway twin bed -stocked kitchen w/blender & toaster -AT&T fiber wifi -wine fridge -smart tv -desk workstation -Levoit air purifier -coffee & tea -happy live plants -inviting neighborhood

Guest favourite

Guest suite in Louisville

4.93 out of 5 average rating, 216 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

Flat in Louisville

4.98 out of 5 average rating, 254 reviews

Spacious & Artsy Highlands 3 Bedroom for Up to 6

There is more room than meets the eye in this surprisingly spacious and uniquely designed space! The lower level of our house (technically the basement) is designed to be an apartment, offering 1400 sq. ft. of relaxing and spacious fun. This is a great space and value for up to six people. The space is closed off from the rest of the house with total privacy. We’re located in a quiet neighborhood in the Highlands and conveniently located to a diverse set of restaurants, highways and grocery.

Guest favourite

Guest house in Jeffersonville

4.88 out of 5 average rating, 182 reviews

The Cottage Next Door

This charming open concept cottage has all the amenities including full kitchen, laundry, one bedroom with in suite full bath, patio, parking, fire pit, WiFi and so much more. You’ll love this place because of the ambiance, privacy, outdoor space, people and location. A lovely space to unwind and relax after a busy day whether it is work or play. We are a short 10/15 minutes drive to Louisville, Ky. Shared driveway, two parking spaces available. We do not allow pets.

Guest favourite

Guest house in Louisville

4.91 out of 5 average rating, 454 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 favourite

Guest suite in Prospect

4.97 out of 5 average rating, 176 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

Guest house in Louisville

4.97 out of 5 average rating, 115 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 favourite

Flat in Louisville

4.99 out of 5 average rating, 123 reviews

Urban Bourbon Farm Loft

Very unique second story 575sqft. duplex apartment with lots of amenities! A 15-20 minutes walk to reservoir park, swim club ($5.00), Blue Dog bakery, restaurants, coffee shops, salons, art galleries, a bookstore, and unique shops! The apartment is a 7 minute walk to the Southern Baptist Theological Seminary, which is a beautiful space to walk and enjoy. This is a second story apartment that is accessible through the backyard privacy fence gate.

Guest favourite

Home in Louisville

4.95 out of 5 average rating, 116 reviews

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

Guest favourite

Farm stay in Goshen

4.98 out of 5 average rating, 291 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....