Vacation rentals in Windy Hills

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Top-rated vacation rentals in Windy Hills

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 151 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.

Jun 26 – Jul 3

ﺩ.ﺇ552 per night

Guest favorite

Home in Jeffersonville

4.95 out of 5 average rating, 152 reviews

Cheerful 2 bedroom home, close to downtown

2 bedroom home & 1.5 bath. Fenced private courtyard. Walk to parks, dining & shopping in downtown Jeffersonville. Across the bridge from Louisville! Lots of light, chef's kitchen w kitchen wares and expandable dining table. 2 bedrooms (queen beds), and a comfy couch. Street parking w designated spot. We live on the street & use a security camera to confirm your arrival, departure, # of reserved guests. Non Smoking home. 8 min drive: Yum!Center/Convention Center/Bourbon distilleries/ restaurants

Sep 4 – 11

ﺩ.ﺇ396 per night

Guest favorite

Townhouse in Louisville

4.95 out of 5 average rating, 211 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

Oct 29 – Nov 5

ﺩ.ﺇ478 per night

Guest favorite

Guest suite in Louisville

4.93 out of 5 average rating, 209 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.

Dec 11 – 18

ﺩ.ﺇ276 per night

Guest favorite

Home in Louisville

4.85 out of 5 average rating, 164 reviews

Private EAST END gem, minutes from 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.

Jun 19 – 26

ﺩ.ﺇ291 per night

Guest favorite

Guesthouse in Jeffersonville

4.88 out of 5 average rating, 180 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.

Jul 16 – 23

ﺩ.ﺇ394 per night

Guest favorite

Guesthouse in Louisville

4.91 out of 5 average rating, 450 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/

Sep 4 – 11

ﺩ.ﺇ237 per night

Guest favorite

Guest suite in Prospect

4.97 out of 5 average rating, 169 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.

Jun 19 – 26

ﺩ.ﺇ523 per night

Guest favorite

Guesthouse in Louisville

4.97 out of 5 average rating, 112 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.)

Aug 27 – Sep 3

ﺩ.ﺇ466 per night

Guest favorite

Guest suite in Louisville

4.95 out of 5 average rating, 288 reviews

Highlands Lower Level Studio Guest Suite

Private, well-lit, entrance is in rear of home. The space is approx. 600sq. ft. There is a gas fireplace, 42" HD TV w/Netflix & Amazon Prime. Kitchen has Keurig coffee maker, convection oven, inferred glass top burner, microwave, refrigerator/freezer w/ice, washer/dryer& a large marble shower, with heated floors in the shower room. Also space equipped w/ Medify air purifier w/H13 true Hepa medical grade filter.

Mar 23 – 30

ﺩ.ﺇ309 per night

Guest favorite

Farm stay in Goshen

4.98 out of 5 average rating, 286 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....

Dec 28 – Jan 4

ﺩ.ﺇ419 per night

Guest favorite

Guesthouse in Louisville

4.93 out of 5 average rating, 785 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 front of the garage. Pets are welcome, plz add them when booking.

Jun 3 – 10

ﺩ.ﺇ331 per night