Windy Hills Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
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Where to stay in Windy Hills
Find the best Windy Hills areas and neighborhoods for the activities you enjoy most. Learn more about Windy Hills
Downtown Louisville
3 out of top 10 points of interest in this area
Explore "Museum Row" in the West Main District, catch a game at Louisville Slugger Field, or stroll across the pedestrian-only Big Four Bridge. Enjoy diverse attractions, restaurants, and the Louie Link skywalk.
St. Matthews
Major shopping destination with the fifth-largest mall in Kentucky, Mall St. Matthews, and smaller centers along Shelbyville Road. Don't miss the historic St. Matthew's Episcopal Church and Holy Trinity.
Old Louisville
Boasting Victorian architecture and the highest concentration of stained glass windows in residential homes, Old Louisville offers a walkable neighborhood with pedestrian-only streets, diverse dining options, and attractions like Central Park and the Conrad-Caldwell House.
Fairgrounds
1 out of top 10 points of interest in this area
While visiting Fairgrounds, you might make a stop by sights like Freedom Hall and Kentucky Kingdom.
Jeffersontown
Jeffersontown is known for its abundant dining options, and you can plan a trip to Jeffersontown Commons Shopping Center and Bluegrass Indoor Karting while you're in town.
Windy Hills Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
￥21,334
￥25,100 total
Nov 8 - Nov 9
includes taxes & fees
9/10 Wonderful! (4,411 reviews)
"The downtown riverside area is a short walk."
Reviewed on Oct 23, 2026
The Brown Hotel
335 W Broadway Louisville KY
Fully refundableReserve now, pay when you stay
￥18,308
￥21,540 total
Nov 23 - Nov 24
includes taxes & fees
9.4/10 Exceptional! (1,414 reviews)
"Perfect location for a show. Breakfast service slow"
Reviewed on Oct 23, 2026
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
￥14,026
￥16,502 total
Nov 15 - Nov 16
includes taxes & fees
9.4/10 Exceptional! (2,584 reviews)
"Our stay was fantastic. We stayed in one of the large king suites and it was the size of a small house. The separate living area with another TV and large sectional was nice. Also for our room, they should note that the derby has practice from 5am until 10am. One of the windows faced the track and ..."
Reviewed on Oct 23, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Windy Hills vacation package cost?
Live it up in Windy Hills from as low as . We offer a wonderful selection of flights, hotels and rental cars to suit every style and budget. Pick up even more discounts when you add a couple of tours or activities to your package.
How do I get a cheap travel package to Windy Hills?
Combine your flight and hotel bookings, toss in extras such as a rental car or activities, and save with a Windy Hills vacation package. You won't just score big discounts on your adventure — you'll have plenty of choice within your reach too. When you book through Expedia, you can choose from more than 550 partner airlines and 1,000,000 hotels around the world. Your affordable vacation starts right here, right now!
Where should I stay in Windy Hills?
Stay where the action happens. Many people like to book hotels within easy reach of top attractions, such as Mall St. Matthews, Baptist Hospital Louisville and Norton Womens & Childrens Hospital.
How far in advance should I book my Windy Hills vacation?
Reserving your seat early with Expedia means one less thing to worry about. Many air carriers display prices up to 12 months prior to departure dates. This is usually the cheapest time to book. If circumstances have left you booking late, discount prices to Windy Hills are still known to appear just a few weeks before departure.
What does an Expedia Windy Hills travel package include?
Select from any combination of hotels, rental cars and flights. Once you've made your booking, you can add some experiences and activities. Want to pick your fare class? That's easily done too. The choice is yours when it comes to arranging your ideal Windy Hills escape.
What should I know before booking a Windy Hills travel package?
You'll pick up big savings when you bundle your hotels, flights and rental cars into a package. Plus, booking everything together simply makes planning easier. So why waste time or money? Whether you're putting together a fancy romantic getaway or a budget solo adventure, check out our vacation packages today.
Can I choose my airline with a Windy Hills Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you sure can! Just choose your preferred carrier and create the perfect Windy Hills getaway.
If I'm not able to travel, can I cancel my Windy Hills vacation package?
Yes, it's possible to cancel your Windy Hills booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
Stay near popular Windy Hills attractions
Brownsboro Center Shopping Center
You can search for that perfect souvenir at Brownsboro Center Shopping Center during your visit to Louisville. Stroll along the riverfront or attend a sporting event in the area.
Things to do
Kentucky Derby Museum - General Admission and Guided Track Visit
￥3,765
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
￥20,238
per adult
94% of travellers recommend
General Admission Ticket to Frazier History Museum
￥2,510
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.