Southside Vacations from $442

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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.

The Latest Southside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Louisville Airport

Hilton Garden Inn Louisville Airport

3 out of 5
Fairgrounds
Price was $658, price is now $442 per person
$442
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,008 reviews)
Shuttle service was great. Kim from hotel staff front desk was excellent. She was friendly, helpful and offered terrific suggestions on dining and local activities in the area.

Reviewed on Oct 2, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was $690, price is now $455 per person
$455
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (821 reviews)
We stayed here for the Louder Than Life festival. Easy check in, room was nice size and very clean. Staff we encountered the entire weekend were very friendly and courteous. We did have an issue as our air conditioning unit stopped working. Maintenance was super prompt and friendly. They had to swap in a new unit which only took about 20 minutes total to diagnose and replace. Amazing really. Will definitely stay here again!

Reviewed on Sep 30, 2025

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
Downtown Louisville
Price was $688, price is now $474 per person
$474
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (3,617 reviews)
The property was centrally located and there were many restaurants and museums near this hotel.

Reviewed on Oct 2, 2025

5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

3 out of 5
Save 100% on your flight
Price was $1,278, price is now $902 per person
$902
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
No reviews
The Grady

The Grady

4 out of 5
Downtown Louisville
Price was $1,069, price is now $765 per person
$765
per person
Nov 7 - Nov 12
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Louisville (SDF)
9.4/10 Exceptional! (1,004 reviews)
Beautiful clean room. Valet attendants the young man during the day he was awesome. Room attendant came to our room to clean she was very pleasant and gave us everything we needed. Really did not see many guests maybe 4 in total so it was very peaceful and quiet.

Reviewed on Sep 30, 2025

Where to stay in Southside

Find the best Southside areas and neighborhoods for the activities you enjoy most. Learn more about Southside
Louisville showing signage and street scenes as well as a small group of people

Downtown Louisville

3 out of top 10 points of interest in this area
4/5(1,812 area reviews)

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
$137 nightly
The price is $161 total per night from Nov 1 to Nov 2
$161 total
Nov 1 - Nov 2
Total with taxes and fees
8.8/10 Excellent! (3,658 reviews)
"Very happy with my stay at The Galt House. We will definitely be back! 💖"

Reviewed on Sep 29, 2025

Galt House Hotel Trademark Collection by Wyndham
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street, Louisville, KY
$199 nightly
The price is $234 total per night from Oct 19 to Oct 20
$234 total
Oct 19 - Oct 20
Total with taxes and fees
9.2/10 Wonderful! (1,625 reviews)
"We enjoyed our stay. The staff at the front desk were very friendly and helpful. Our room was comfy, loved the shower. There were several choices for dinner within walking distance."

Reviewed on Sep 29, 2025

Omni Louisville Hotel
Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
4520 Poplar Level Rd, Louisville, KY
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Oct 5 to Oct 6
$140 total
Oct 5 - Oct 6
Total with taxes and fees
9.4/10 Exceptional! (1,485 reviews)
"My room and the staff were absolutely amazing. This is my second time staying at this hotel and it never disappoints. One thing that I didn’t realize is that you have to request housekeeping services if you are staying for several days. No fault of the hotels though. I just didn’t know. However, ..."

Reviewed on Oct 1, 2025

Derby City Gaming & Hotel - A Churchill Downs Property
See all 2,000 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Southside

Ky Derby festival balloon glow.

Kentucky Exposition Center

Learn about the events happening at Kentucky Exposition Center during your trip to Louisville. Experience the area's acclaimed art scene and great live music.

Kentucky Exposition Center
Churchill Downs showing horseriding and land animals as well as a small group of people

Churchill Downs

Find more than mint juleps to enjoy at this iconic racetrack, best known as the annual host of the Kentucky Derby.

Churchill Downs
Louisville Slugger Museum showing interior views

Louisville Slugger Museum

Baseball is part of the American fabric. See where one important tool for this sport is produced in the factory that makes ball games possible.

Louisville Slugger Museum

Things to do

Kentucky Derby Museum - Admission with Guided Track Visit

Kentucky Derby Museum - Admission with Guided Track Visit

$22
per adult
Kentucky Derby Museum - Admission with Guided Track Visit
Derby City Ghosts: Louisville Hauntings Tour

Derby City Ghosts: Louisville Hauntings Tour

$32
per adult
Derby City Ghosts: Louisville Hauntings Tour
Smartphone-Guided Walking Tour of Downtown Louisville Sights & Stories

Smartphone-Guided Walking Tour of Downtown Louisville Sights & Stories

$15
per traveler
Smartphone-Guided Walking Tour of Downtown Louisville Sights & Stories
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.