Windy Hills Vacation Packages

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  • Better together

    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.
Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was CA $1,156, price is now CA $977 per person
CA $977
per person
Jan 27 - Jan 31
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Louisville (SDF)
8.8/10 Excellent! (1,012 reviews)

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was CA $1,581, price is now CA $1,239 per person
CA $1,239
per person
Jan 27 - Jan 31
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
Housekeeping knocked

Reviewed on Nov 8, 2026

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was CA $1,910, price is now CA $1,586 per person
CA $1,586
per person
Jan 27 - Jan 31
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Louisville (SDF)
9.6/10 Exceptional! (511 reviews)
Excellent location and room!

Reviewed on Nov 6, 2026

The Grady

The Grady

4 out of 5
Downtown Louisville
Price was CA $1,429, price is now CA $1,219 per person
CA $1,219
per person
Jan 27 - Jan 31
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Louisville (SDF)
9.4/10 Exceptional! (1,003 reviews)
Would definitely stay here again.

Reviewed on Nov 8, 2026

Holiday Inn Express Louisville Airport Expo Center by IHG

Holiday Inn Express Louisville Airport Expo Center by IHG

2.5 out of 5
Hayfield Dundee
Price was CA $1,141, price is now CA $986 per person
CA $986
per person
Jan 27 - Jan 31
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Louisville (SDF)
8.6/10 Excellent! (1,005 reviews)
Check in was great and fast.The room was nice and clean.The breakfast was above average.Also my daughter flew in from Houston and the staff picked her up with the shuttle from the airport with no problem

Reviewed on Nov 8, 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

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.

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
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Nov 22 to Nov 23
CA $192
CA $226 total
Nov 22 - Nov 23
includes taxes & fees
9/10 Wonderful! (4,479 reviews)
"The best hotel in Louisville. Very clean room, helpful staff especially Rico & accessible."

Reviewed on Nov 9, 2026

Galt House Hotel Trademark Collection by Wyndham
The Brown Hotel

The Brown Hotel

4.5 out of 5
335 W Broadway Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Nov 25 to Nov 26
CA $147
CA $173 total
Nov 25 - Nov 26
includes taxes & fees
9.4/10 Exceptional! (1,467 reviews)
"The breakfast was lively. The building beautiful. Lovely big room"

Reviewed on Nov 8, 2026

The Brown Hotel
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

4 out of 5
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Nov 17 to Nov 18
CA $131
CA $154 total
Nov 17 - Nov 18
includes taxes & fees
9.6/10 Exceptional! (2,621 reviews)
"Hermosa habitación, espaciosa, un buen baño y muy elegante"

Reviewed on Nov 9, 2026

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
See all 2,115 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 $977. 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 $182
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
Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour

Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour

CA $14
per adult
80% of travellers recommend
Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour
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.