Windy Hills Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Windy Hills Vacation

The easiest way to experience this city is with a tailor-made Windy Hills vacation package. Base yourself in the neighborhood of East Market District, which is good for nightlife, distilleries and craft breweries and shopping or choose someplace else — our packages are all about you. If taking in sights is part of the program during your trip to Windy Hills, stop by popular attractions like E.P. Tom Sawyer State Park, Mall St. Matthews and Springhurst Towne Center Shopping Center. Browse Expedia's wide range of travel options and start planning your ideal vacation to Windy Hills today.

Top Holiday Package Deals in Windy Hills

Price found within the past 48 hours. Click for updated prices.
Louisville Marriott Downtown

Louisville Marriott Downtown

Downtown Louisville
CA $1,107
per person
Oct 23 - Oct 25
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
Omni Louisville Hotel

Omni Louisville Hotel

Downtown Louisville
CA $1,811
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Louisville (SDF)
9.4/10 Exceptional! (2,094 reviews)
Clean room.

Reviewed on Sep 2, 2026

Embassy Suites Louisville Downtown

Embassy Suites Louisville Downtown

Downtown Louisville
CA $1,600
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Louisville (SDF)
9/10 Wonderful! (1,347 reviews)
Excellent workers very good experience

Reviewed on Sep 2, 2026

The Bellwether Hotel

The Bellwether Hotel

Tyler Park
CA $1,529
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Louisville (SDF)
9/10 Wonderful! (54 reviews)
Holiday Inn Louisville Downtown by IHG

Holiday Inn Louisville Downtown by IHG

Downtown Louisville
CA $1,426
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Louisville (SDF)
8/10 Very good! (995 reviews)
My stay started off rough with ants and dirty walls. Management stepped in and changed my room and it was much better. The hotel is in a good location. I thinks it needs some updates to bring it into modern day. Thank you staff for fast thinking.

Reviewed on Sep 2, 2026

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
A city skyline with various buildings, including a prominent KFC and a green-roofed structure.

Downtown Louisville

4 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.

Find hotels in Downtown Louisville
A brown horse with a red halter, a person in a black shirt, and a crowd of people in the background.

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.

Find hotels in Fairgrounds
A city skyline at dusk with illuminated buildings reflecting on the water.

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.

Find hotels in Jeffersontown
A nighttime cityscape with a brightly lit bridge and a skyline featuring a prominent dome-shaped building.

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.

Find hotels in St. Matthews
A narrow stream with a rocky bridge, surrounded by trees and greenery.

Phoenix Hill

While Phoenix Hill isn't home to many top sights, Nulu Market Place and Louisville Slugger Field are some notable places to visit nearby.

Find hotels in Phoenix Hill

Windy Hills Hotel Deals

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
CA $221
CA $260 total
Sep 4 - Sep 5
includes taxes & fees
Galt House Hotel Trademark Collection by Wyndham
Holiday Inn Express & Suites Louisville Downtown by IHG

Holiday Inn Express & Suites Louisville Downtown by IHG

800 W Market St Louisville KY
Fully refundableReserve now, pay when you stay
CA $135
CA $158 total
Sep 4 - Sep 5
includes taxes & fees
8.8/10 Excellent! (1,784 reviews)
"The room wasn’t so clean , the plugs were loose, stuff wasn’t so welcoming"

Reviewed on Sep 2, 2026

Holiday Inn Express & Suites Louisville Downtown by IHG
Omni Louisville Hotel

Omni Louisville Hotel

400 S. 2nd Street Louisville KY
Fully refundableReserve now, pay when you stay
CA $273
CA $321 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (2,106 reviews)
"Clean room."

Reviewed on Sep 2, 2026

Omni Louisville Hotel
See all 2,146 properties in Windy Hills
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.
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Frequently asked questions

How much does a Windy Hills vacation package cost?
Live it up in Windy Hills from as low as CA $1,107. 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.
See properties

Things to do

Louisville: 3-Hour Food and History Tour of NuLu District

Louisville: 3-Hour Food and History Tour of NuLu District

CA $179
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

CA $28
per adult
94% of travellers recommend
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
General Admission Ticket to Frazier History Museum

General Admission Ticket to Frazier History Museum

CA $22
per adult
General Admission Ticket to Frazier History Museum
See all activities in Louisville
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.