Highlands Vacations from $527

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Your Highlands Vacation

Make travel planning hassle-free by creating a vacation package to Highlands. We'll handle the finer points, so you can focus on soaking up everything this neighborhood has to offer. Your trip to Highlands wouldn't be complete without a stop at big-name attractions nearby such as Muhammad Ali Center, KFC Yum Center and University of Louisville. Expedia will help put your plans into action. Book your perfect Highlands vacation now.

The Latest Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
stayAPT Suites Louisville North-Clarksville

stayAPT Suites Louisville North-Clarksville

$527
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9.8/10 Exceptional! (56 reviews)
Great option for a long term stay, good area many businesses in walking distance!

Reviewed on Sep 22, 2026

The Purple Martin

The Purple Martin

$767
per person
Dec 2 - Dec 6
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
10/10 Exceptional! (2 reviews)
Amazing property… I would come back in a heartbeat!

Reviewed on Jun 19, 2025

Pillow and Paddock B&B

Pillow and Paddock B&B

Save 100% on your flight
$978
per person
Dec 2 - Dec 6
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
10/10 Exceptional! (52 reviews)
Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it.

Reviewed on Dec 22, 2025

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

Downtown Louisville
$865
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9.6/10 Exceptional! (505 reviews)
Great hotel, right in the middle of the city.

Reviewed on Sep 27, 2026

The Duke Hotel

The Duke Hotel

Downtown Louisville
$556
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.2/10 Very Good! (23 reviews)
Check in was difficult because there are two separate buildings and I was not given a room number or door code or instructions about which building I was supposed to be in. The hotel spammed my email with literally 18 messages most of which were redundant and others which had links that didn’t work. The actual room was fine and in a nice area. Unfortunately for me, my particular room was directly above a bar that played loud thumping music past 2:30 in the morning on a Monday. I asked the bar if they would turn it down but they didn’t care and acted like I was crazy for asking. I couldn’t sleep. They should never put guests in this room. Parking is included but you have to register with the adjacent lot which requires you pay a fee which will be refunded eventually. They didn’t refund my fee and actually charged me an additional fee which I didn’t authorize. It took a lot of time and patience to get them to refund both charges. This place ruined my stay in Louisville, and further troubled me after I got home. I think Expedia should take them off their listing. 0/10.

Reviewed on Sep 19, 2026

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
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.

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.

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.

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.

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.

Highlands 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
$150 nightly
$177 total
Oct 31 - Nov 1
Total with taxes and fees
Galt House Hotel Trademark Collection by Wyndham
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

830 Phillips Lane Louisville KY
Fully refundable
$101 nightly
$119 total
Oct 25 - Oct 26
Total with taxes and fees
Crowne Plaza Louisville Airport Expo Ctr by IHG
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
$103 nightly
$121 total
Oct 30 - Oct 31
Total with taxes and fees
8.8/10 Excellent! (1,820 reviews)
"The room and bed were very comfortable. The only thing that needs improvement is the breakfast food. The eggs were dry every day; the sausages didn't taste good. The juices were too watered down. One day the cereal tasted stale. The buffet comes with the room; however, you'd be better off eating ..."

Reviewed on Sep 30, 2026

Holiday Inn Express & Suites Louisville Downtown by IHG
See all 2,143 properties in Highlands
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.

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.