Southside Vacation Packages

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Your Southside Vacation

Take away the hard part of planning your next epic adventure with a Southside vacation package. Whether you're here for its food, history, art or other highlights, this city offers endless possibilities for fun. If a sightseeing tour is on the cards during your trip to Southside, stop by major attractions like Churchill Downs, Muhammad Ali Center and KFC Yum Center. No matter your travel plans or the size of your budget, organizing your ultimate tailored Southside vacation is a walk in the park with Expedia.

Top Holiday Package Deals in Southside

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was CA $1,165, price is now CA $922 per person
CA $922
per person
Jan 6 - Jan 10
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
Right at the fourth street. Walking to pubs and restaurants. Very nice room. Would stay here again.

Reviewed on Oct 31, 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was CA $1,171, price is now CA $940 per person
CA $940
per person
Jan 6 - Jan 10
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,012 reviews)
Great stay. Staff was very nice and clean room. Breakfast area was a little small and crowded. Other than that I would definitely stay here again.

Reviewed on Oct 31, 2026

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was CA $1,269, price is now CA $1,041 per person
CA $1,041
per person
Jan 6 - Jan 10
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,902 reviews)
The building from the outside and lobby looks beautiful, but when you go to your room it's out dated the sheets are so thin you can see the pattern on the mattress through them and the beds are lumpy. I've stayed at other crown plazas and the rooms were nicer .

Reviewed on Nov 1, 2026

Holiday Inn Express Louisville Airport Expo Center by IHG

Holiday Inn Express Louisville Airport Expo Center by IHG

2.5 out of 5
Hayfield Dundee
Price was CA $1,107, price is now CA $925 per person
CA $925
per person
Jan 6 - Jan 10
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.6/10 Excellent! (1,005 reviews)
Excelente servicio

Reviewed on Oct 31, 2026

Holiday Inn Louisville Airport South by IHG

Holiday Inn Louisville Airport South by IHG

3 out of 5
Price was CA $1,115, price is now CA $932 per person
CA $932
per person
Jan 6 - Jan 10
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)

Where to stay in Southside

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

Southside 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
The price is CA $190 per night from Nov 15 to Nov 16
CA $190
CA $224 total
Nov 15 - Nov 16
includes taxes & fees
9/10 Wonderful! (4,451 reviews)
"Great place to relax friendly staff"

Reviewed on Nov 1, 2026

Galt House Hotel Trademark Collection by Wyndham
The Brown Hotel

The Brown Hotel

4.5 out of 5
335 W Broadway Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Nov 25 to Nov 26
CA $146
CA $172 total
Nov 25 - Nov 26
includes taxes & fees
The Brown Hotel
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

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

4 out of 5
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Nov 9 to Nov 10
CA $125
CA $147 total
Nov 9 - Nov 10
includes taxes & fees
9.4/10 Exceptional! (2,594 reviews)
"Beautiful cleanroom staff is amazing. Hotel is spectacular. The casino i give it a 8"

Reviewed on Oct 31, 2026

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
See all 2,093 properties in Southside
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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Southside vacation package cost?
Handcraft your Southside package from an affordable CA $922. 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.

Things to do

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

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

CA $182
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

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

CA $28
per adult
94% of travellers recommend
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour

Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour

CA $14
per adult
80% of travellers recommend
Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour
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.