Windy Hills Vacation Packages

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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.
Caesars Southern Indiana

Caesars Southern Indiana

3.5 out of 5
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8.2/10 Very Good! (1,007 reviews)
Very nice place would stay here again

Reviewed on Apr. 5, 2025

5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

3 out of 5
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
No reviews
Hotel Genevieve

Hotel Genevieve

4 out of 5
Downtown Louisville
per person
Jul. 9 - Jul. 16
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9.2/10 Wonderful! (737 reviews)
Nice, quirky, great staff. They don't offer enough services, though. Its6the first hotel I've every been to that didn't have a gym.

Reviewed on Apr. 21, 2025

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9.6/10 Exceptional! (373 reviews)
Nice place to stay.

Reviewed on Mar. 18, 2025

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
Great location and beautiful hotel . The porch restaurant is fabulous !

Reviewed on Apr. 19, 2025

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
Louisville showing signage and street scenes as well as a small group of people

Downtown Louisville

3 out of top 10 points of interest in this area
4/5(37 area reviews)

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

Windy Hills Hotel Deals

Galt House Hotel Trademark Collection by Wyndham
Galt House Hotel Trademark Collection by Wyndham
4 out of 5
140 North Fourth Street, Louisville, KY
The price is CA $210 per night from May 22 to May 23
CA $210
CA $247 total
includes taxes & fees
May 22 - May 23
8.8/10 Excellent! (3,330 reviews)
"Always an enjoyable stay at the Galt house."

Reviewed on Apr. 18, 2025

Galt House Hotel Trademark Collection by Wyndham
Crowne Plaza Louisville Airport Expo Ctr by IHG
Crowne Plaza Louisville Airport Expo Ctr by IHG
3.5 out of 5
830 Phillips Lane, Louisville, KY
The price is CA $117 per night from May 19 to May 20
CA $117
CA $137 total
includes taxes & fees
May 19 - May 20
8.6/10 Excellent! (426 reviews)
"Shenna at the front desk was extremely helpful, friendly and professional. Dinner at Big Al’s was delicious and very well priced. The hotel is beautiful and the transportation to the airport couldn’t be more convenient. Highly recommend!"

Reviewed on Apr. 20, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG
Omni Louisville Hotel
Omni Louisville Hotel
4 out of 5
400 S. 2nd Street, Louisville, KY
The price is CA $254 per night from May 8 to May 9
CA $254
CA $299 total
includes taxes & fees
May 8 - May 9
9/10 Wonderful! (1,411 reviews)
"We loved our stay at the Omni Louisville! Great walkability & staff was super helpful. Love the speakeasy in the lobby too! Highly recommend & plan to return!"

Reviewed on Apr. 20, 2025

Omni Louisville Hotel
See all 1,994 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Windy Hills vacation package cost?
Live it up in Windy Hills from as low as CA $613. 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.

Discover the most popular places to visit in Windy Hills

Kentucky Exposition Center

Kentucky Exposition Center

4.5/5(14 reviews)

During your trip, find out what's happening at Kentucky Exposition Center, a top convention center in Louisville. Experience the area's acclaimed theater scene and lively festivals.

Kentucky Exposition Center
Churchill Downs showing land animals and horse riding as well as a small group of people

Churchill Downs

4.5/5(22 reviews)

Find more than mint juleps to enjoy at this iconic racetrack, best known as the annual host of the Kentucky Derby.

Churchill Downs
Louisville Slugger Museum featuring interior views

Louisville Slugger Museum

4.5/5(18 reviews)

Baseball is part of the American fabric. See where one important tool for this sport is produced in the factory that makes ball games possible.

Louisville Slugger Museum

Things to do

Derby City Ghosts: Louisville Hauntings Tour

Derby City Ghosts: Louisville Hauntings Tour

CA $37
per adult
Derby City Ghosts: Louisville Hauntings Tour
Louisville: NuLu District Food and History Tour

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

CA $186
per adult
Louisville: 3-Hour Food and History Tour of NuLu District
Louisville: Photoshoot Walking Tour with Pictures

Louisville: Photoshoot Walking Tour with Pictures

CA $79
per adult
Louisville: Photoshoot Walking Tour with Pictures
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.