Highlands Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

The cultural heart of the city beats with baseball, boxing and music, with sporting fields, live bands and a center for Muhammad Ali, the city’s most famous son.

Find hotels in Downtown Louisville
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 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.

Find hotels in Jeffersontown
A nighttime cityscape with a brightly lit bridge and a skyline featuring a prominent dome-shaped building.

St. Matthews

St. Matthews is noteworthy for its shopping, and you can make a stop at top attractions like Mall St. Matthews and Saint Matthews Pavilion Shopping Center.

Find hotels in St. Matthews
A narrow stream with a rocky bridge, surrounded by trees and greenery.

Phoenix Hill

While Phoenix Hill isn't home to many top sights, Nulu Market Place and Louisville Slugger Field are some notable places to visit nearby.

Find hotels in Phoenix Hill

Top hotels in Highlands

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
S$215
20 Aug - 21 Aug
includes taxes & fees
9/10 Wonderful! (4,262 reviews)
"A"

Reviewed on 11 Aug, 2026

Galt House Hotel Trademark Collection by Wyndham
Omni Louisville Hotel

Omni Louisville Hotel

400 S. 2nd Street Louisville KY
Fully refundableReserve now, pay when you stay
S$239
16 Aug - 17 Aug
includes taxes & fees
Omni Louisville Hotel
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

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

4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
S$165
19 Aug - 20 Aug
includes taxes & fees
9.4/10 Exceptional! (2,420 reviews)
"The rooms are very spacious and clean!"

Reviewed on 10 Aug, 2026

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
See all 2,101 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.

Frequently asked questions

How much does a Highlands holiday package cost?
Cross off another part of the world with our Highlands holiday packages, which start from a low . Select the flights and hotels that suit your style. Then, add on one or two experiences or tours to cap off your unique getaway.
How do I get a cheap travel package to Highlands?
It's as simple as bundling. Hotels, flights and rental cars — combine whatever you need into a Highlands holiday package to save tons of cash. Score even more bargains when you include extras such as day tours to your booking. But that's not the only good part. You have the freedom to customize your holiday your way. We offer more than 550 partner airlines and 1,000,000 hotel options worldwide, so that everyone has a chance to travel and fulfil those holiday dreams.
How far in advance should I book my Highlands holiday?
It all depends on the air carrier, but it's usually possible to look up international airfares on Expedia nearly a year in advance. While it's a good idea to book ahead of time, lucky travellers will occasionally nab a cheaper ticket just weeks before the date of departure.
What does an Expedia Highlands travel package include?
It depends on what kind of trip you have in the works. Highlands holiday deals can include hotels, car rentals and flights. You can mix and match to create the package that suits your budget and style. You can also add on activities and experiences after you've booked to get even bigger discounts.
What should I know before booking a Highlands travel package?
You can save a tidy sum by combining your hotels, flights and rental cars. Once you've created your package, you can add on things like sightseeing tours or experiences. Your next unforgettable holiday is only a few clicks away.
Can I choose my airline with a Highlands Expedia holiday package?
Yes, you sure can. We offer more than 550 partner airlines all over the world, so choose the carrier that matches your travel preferences.
If I'm not able to travel, can I cancel my Highlands holiday package?
It's good to know that you can cancel your Highlands booking if your travel plans have changed. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

Things to do

Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

S$26
per adult
92% of travellers recommend
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
Louisville: 3-Hour Food and History Tour of NuLu District

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

S$166
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
General Admission Ticket to Frazier History Museum

General Admission Ticket to Frazier History Museum

S$21
per adult
General Admission Ticket to Frazier History Museum
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.