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.

Guest favorite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 149 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.

Dec 7 – 14

G$30,472 GYD per night
Guest favorite

Townhouse in Louisville

4.95 out of 5 average rating, 209 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

Jun 28 – Jul 5

G$25,978 GYD per night
Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 103 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.

Jul 5 – 12

G$18,375 GYD per night

Popular amenities for Windy Hills vacation rentals

Stay near Windy Hills's top sights

Panera Bread9 locals recommend
Noosh Nosh9 locals recommend
Anoosh Bistro12 locals recommend

Other great vacation rentals in Windy Hills

Guest favorite

Apartment in Louisville

4.95 out of 5 average rating, 597 reviews

Charming Highlands apartment

Dec 31 – Jan 7

G$22,549 GYD per night
Guest favorite

Home in Jeffersonville

4.95 out of 5 average rating, 149 reviews

Cheerful 2 bedroom home, close to downtown

Nov 8 – 15

G$21,269 GYD per night
Guest favorite

Home in Louisville

4.9 out of 5 average rating, 170 reviews

Quiet Neighborhood Home With Outstanding Location

Aug 30 – Sep 6

G$21,853 GYD per night
Guest favorite

Home in Louisville

4.92 out of 5 average rating, 109 reviews

Cheerful, centrally located 2 bedroom shotgun home

Dec 23 – 30

G$22,658 GYD per night
Guest favorite

Home in Louisville

4.95 out of 5 average rating, 146 reviews

The River's Edge Oasis, close to downtown

Jul 7 – 14

G$63,987 GYD per night
Guest favorite

Guest suite in Windy Hills

4.93 out of 5 average rating, 40 reviews

Comfy Getaway Guest Suite in Louisville

Jun 24 – Jul 1

G$21,443 GYD per night
Guest favorite

Apartment in Saint Matthews

5.0 out of 5 average rating, 75 reviews

Swanky Fully Equipped St. Matthews Apartment

Oct 5 – 12

G$23,351 GYD per night
Guest favorite

Guest suite in Louisville

4.96 out of 5 average rating, 28 reviews

Middletown Private Guest House

Apr 22 – 29

G$19,245 GYD per night
Guest favorite

Apartment in Louisville

4.94 out of 5 average rating, 63 reviews

The Dream Location of Louisville

Feb 12 – 19

G$23,047 GYD per night
Guest favorite

Apartment in Saint Matthews

4.95 out of 5 average rating, 85 reviews

cozy two bedroom apartment

Aug 24 – 31

G$26,304 GYD per night
Guest favorite

Cottage in Jeffersonville

4.92 out of 5 average rating, 38 reviews

Peaceful Easy Feeling

Aug 26 – Sep 2

G$26,358 GYD per night
Guest favorite

Guest suite in Saint Matthews

4.93 out of 5 average rating, 70 reviews

The Oxford

Dec 29 – Jan 5

G$30,692 GYD per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Jefferson County
  5. Windy Hills