Windy Hills Vacations from $268

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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.

The Latest Windy Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Louisville Airport by IHG

Candlewood Suites Louisville Airport by IHG

2.5 out of 5
Watterson Park
Price was $324, price is now $268 per person
$268
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip flight included
Washington (WAS) to Louisville (SDF)
8.2/10 Very Good! (330 reviews)
I would stay here again. The room was a little musty and the shower drain was clogged, but besides that it was pretty nice, especially for the price.

Reviewed on Sep 22, 2025

Hampton Inn Louisville-Airport

Hampton Inn Louisville-Airport

2.5 out of 5
Fairgrounds
Price was $355, price is now $296 per person
$296
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip flight included
Washington (WAS) to Louisville (SDF)
8.6/10 Excellent! (1,003 reviews)
Clean room staff treated me well made me feel like I was at home overall great time thanks again

Reviewed on Sep 20, 2025

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $1,075, price is now $924 per person
$924
per person
Oct 30 - Nov 3
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9/10 Wonderful! (1,002 reviews)
Great Hotel. Great restaurant. Great bar.

Reviewed on Sep 16, 2025

Comfort Inn & Suites Louisville Airport Fair & Expo

Comfort Inn & Suites Louisville Airport Fair & Expo

2.5 out of 5
Fairgrounds
Price was $306, price is now $274 per person
$274
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip flight included
Washington (WAS) to Louisville (SDF)
8.2/10 Very Good! (90 reviews)
It was very nice but I did find a little critter in the stairs but other than that it was nice and the beds was really comfy

Reviewed on Sep 27, 2025

DuPont Mansion Bed & Breakfast

DuPont Mansion Bed & Breakfast

3 out of 5
Old Louisville
Price was $401, price is now $360 per person
$360
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip flight included
Washington (WAS) to Louisville (SDF)
9.8/10 Exceptional! (85 reviews)
The perfect combination of old-world charm and modern comforts. The owners have thought of every detail to create a lovely stay, and we loved arriving to a warm welcome of tea and cookies. The rooms are precious and cared for immaculately. May, the hostess and caretaker of the space, was so delightful! So caring of guests. The breakfast was exquisite, and served with love. Thank you, DuPont Mansion!

Reviewed on Sep 14, 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(1,812 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
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $168 total per night from Oct 3 to Oct 4
$168 total
Oct 3 - Oct 4
Total with taxes and fees
8.8/10 Excellent! (3,638 reviews)
"Liked how close it was to everything. Wasn't told about getting a parking pass until we were leaving."

Reviewed on Sep 22, 2025

Galt House Hotel Trademark Collection by Wyndham
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street, Louisville, KY
$199 nightly
The price is $234 total per night from Oct 19 to Oct 20
$234 total
Oct 19 - Oct 20
Total with taxes and fees
9.2/10 Wonderful! (1,623 reviews)
"Upscale stay, beautiful property, and great location! We were able to walk to so many great restaurants and the hotel really made a great experience for our first time in Louisville. Will be returning!"

Reviewed on Sep 21, 2025

Omni Louisville Hotel
Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
4520 Poplar Level Rd, Louisville, KY
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Sep 29 to Sep 30
$140 total
Sep 29 - Sep 30
Total with taxes and fees
9.4/10 Exceptional! (1,456 reviews)
rest after work
"Lots of places to eat within 10 minute drive. Hotel very clean and lots to do without leaving hotel."

Reviewed on Sep 24, 2025

Derby City Gaming & Hotel - A Churchill Downs Property
See all 2,017 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
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Discover the most popular places to visit in Windy Hills

Ky Derby festival balloon glow.

Kentucky Exposition Center

Learn about the events happening at Kentucky Exposition Center during your trip to Louisville. Experience the area's acclaimed art scene and great live music.

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

Churchill Downs

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 showing interior views

Louisville Slugger Museum

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

Kentucky Derby Museum - Admission with Guided Track Visit

Kentucky Derby Museum - Admission with Guided Track Visit

$22
per adult
Kentucky Derby Museum - Admission with Guided Track Visit
Derby City Ghosts: Louisville Hauntings Tour

Derby City Ghosts: Louisville Hauntings Tour

$32
per adult
Derby City Ghosts: Louisville Hauntings Tour
Smartphone-Guided Walking Tour of Downtown Louisville Sights & Stories

Smartphone-Guided Walking Tour of Downtown Louisville Sights & Stories

$15
per traveler
Smartphone-Guided Walking Tour of Downtown Louisville Sights & Stories
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.