Southside Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NT$25,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Where to stay in Southside
Find the best Southside areas and neighborhoods for the activities you enjoy most. Learn more about Southside
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.
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.
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.
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.
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.
Southside Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
NT$4,438
NT$5,221 total
Nov 8 - Nov 9
includes taxes & fees
9/10 Wonderful! (4,434 reviews)
"The room was clean and roomy"
Reviewed on 2026/10/26
The Brown Hotel
335 W Broadway Louisville KY
Fully refundableReserve now, pay when you stay
NT$4,408
NT$5,186 total
Nov 23 - Nov 24
includes taxes & fees
9.4/10 Exceptional! (1,427 reviews)
"Kind helpful staff, beautiful architecture"
Reviewed on 2026/10/26
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
NT$3,647
NT$4,291 total
Oct 27 - Oct 28
includes taxes & fees
9.4/10 Exceptional! (2,591 reviews)
"Third visit and have had great food, drinks and service. 5 stars in my book."
Reviewed on 2026/10/26
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 Southside vacation package cost?
Handcraft your Southside package from an affordable . Choose from any combination of hotels, flights and rental cars to craft the trip you've long been dreaming about. Be sure to add on a few experiences or activities!
How do I get a cheap travel package to Southside?
Find flights that fit your schedule, add a hotel room to your booking and watch the savings grow with a Southside vacation package. It's that simple! From hotels and flights to rental cars and activities, Expedia makes traveling cheaply a cinch. And with over 550 partner airlines and 1,000,000 hotel options across the globe to select from, you won't be short of choice.
Where should I stay in Southside?
Most visitors to Southside put both Churchill Downs and Muhammad Ali Center on their to-do lists. Why not book a hotel as close as possible to these top attractions?
How far in advance should I book my Southside vacation?
It depends on the air carrier, but it's usually possible to look up international fares on Expedia up to 12 months in advance. While it's a good idea to book ahead of time, lucky customers occasionally nab a cheaper seat just weeks before the date of departure.
What does an Expedia Southside travel package include?
Rental cars, flights and hotels, or any combination of the three — you decide! Whether you're visiting Southside with the family or adventuring with your friends, there's a package to match every style and budget. Once you've made your booking, why not add on one or two tours as well?
What should I know before booking a Southside travel package?
You can look forward to saving with an Expedia travel package. Combine your flights, rental cars and hotels and enjoy great discounts. Hotels aren't your only choice, though. Book with us and select from beach villas, rural cottages and even treehouses and ranches!
Can I choose my airline with a Southside Expedia vacation package?
You can, and with over 550 airlines to choose from around the world, you have plenty of choice. Take a look at the available options and find out which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Southside vacation package?
Don't worry if you're rethinking your Southside vacation package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We totally understand your circumstances can change suddenly, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we're ready to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.