Windy Hills Vacations from $663

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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.
TownePlace Suites by Marriott Louisville Airport

TownePlace Suites by Marriott Louisville Airport

$663
per person
Dec 23 - Dec 30
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9.2/10 Wonderful! (228 reviews)
Nice spot for an overnight stay.

Reviewed on Oct 5, 2026

The Brown Hotel

The Brown Hotel

Downtown Louisville
$849
per person
Dec 23 - Dec 30
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,333 reviews)
The Grady

The Grady

Downtown Louisville
$819
per person
Dec 23 - Dec 30
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,011 reviews)
Beautiful hotel. Very clean with friendly staff and within walking distance to tons of bars and restaurants

Reviewed on Oct 4, 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

Shively
$693
per person
Dec 23 - Dec 30
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.6/10 Excellent! (1,008 reviews)
Holiday Inn Express & Suites Louisville Downtown by IHG

Holiday Inn Express & Suites Louisville Downtown by IHG

Downtown Louisville
$723
per person
Dec 23 - Dec 30
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (1,819 reviews)

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
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 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.

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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 large, illuminated two-story house with a prominent front porch and a garage.

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.

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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
$145 nightly
$171 total
Oct 25 - Oct 26
Total with taxes and fees
Galt House Hotel Trademark Collection by Wyndham
The Brown Hotel

The Brown Hotel

335 W Broadway Louisville KY
Fully refundableReserve now, pay when you stay
$152 nightly
$179 total
Oct 28 - Oct 29
Total with taxes and fees
The Brown Hotel
Radisson Hotel Louisville North

Radisson Hotel Louisville North

505 Marriott Drive Clarksville IN
Fully refundable
$70 nightly
$79 total
Nov 7 - Nov 8
Total with taxes and fees
Radisson Hotel Louisville North
See all 2,125 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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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

Kentucky Derby Museum

Kentucky Derby Museum - General Admission and Guided Track Visit

$24
per adult
94% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
Louisville: 3-Hour Food and History Tour of NuLu District

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

$129
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby

Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby

$29
per adult
92% of travellers recommend
Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby
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.