Jackson Vacations from $592

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Your Jackson Vacation

Book a Jackson vacation package and immerse yourself in the rhythm and vibe of this sought-after neighborhood. With all your travel plans worked out, the only thing you need to focus on here is having an absolute ball. Not sure what to see and do during your trip to Jackson? Nearby attractions such as Muhammad Ali Center, KFC Yum Center and University of Louisville are great places to start. Expedia can put your plans into action. Book your ultimate Jackson vacation now.

The Latest Jackson Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Regina's Country Livin'

Regina's Country Livin'

$592
per person
Oct 19 - Oct 24
found 20 hours ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)
10/10 Exceptional! (10 reviews)
For my first time visiting in Kentucky, I’m glad I picked to stay at Regina’s Country Living. Hostess : Top notch hospitality; Regina looked out for everyone who stayed for the Kentucky Derby event like a mother. Our breakfast was homemade each morning, and it definitely brought back memories with of my grandma for Sunday and Christmas breakfast specials. Room/Home : Regina’s home had so much old southern world charm that had it not been so cool outside, that drinking a Mint Julep on the porch would have been a pleasant experience. I stayed in the “ King’s Room “, my bed was huge and the covers were soft and inviting. I slept good everyday I was there and I slept really good after the Derby. Each room had a story to tell and I’d especially liked the sky light in the family room. The park adjacent to the house is such a nice addition for anyone who just wants to take a walk or run. It’s perfect if you bring a dog with you on your stay as well. Thank you, Regina for opening up your home and being an amazing woman. Thank you for sharing an amazing friendly dinner with me at the Mexican restaurant and making sure a solo traveler felt like family even if it was for a few days. Looking forward to next year’s Kentucky Derby at your Bed and Breakfast.

Reviewed on May 4, 2026

Louisville Marriott Downtown

Louisville Marriott Downtown

Downtown Louisville
Save 100% on your flight
$1,235
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
Property was nice! Room was as expected! Valet/service was much to be desired! Room service snd bar service was some of the worst I’ve ever encountered! Was told by room service they had water; but if I wanted then I had to come get them myself! She wasn’t delivering them! Bartender in the hotel lounge was so bad it was laughable!! Told us she was doing us a favor by waiting on us! Lost her mind when I ask for 3 small bowls to put nuts in so our party of eight didn’t have to pass around the same cardboard cup she put them in!

Reviewed on Aug 16, 2026

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

Downtown Louisville
$1,337
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.6/10 Exceptional! (491 reviews)
Amazing stay in the heart of whiskey row

Reviewed on Aug 24, 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

Shively
$1,325
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (1,013 reviews)
Clean room and helpful staff. Breakfast options were not enough.

Reviewed on Aug 24, 2026

Moxy Louisville Downtown

Moxy Louisville Downtown

Downtown Louisville
$1,011
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.2/10 Wonderful! (815 reviews)
Loved Moxy. Staff was outstanding. Perfect location. Very quiet for downtown Louisville.

Reviewed on Aug 23, 2026

Where to stay in Jackson

Find the best Jackson areas and neighborhoods for the activities you enjoy most. Learn more about Jackson
A city skyline with various buildings, including a prominent KFC and a green-roofed structure.

Downtown Louisville

5 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 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 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 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.

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.

Jackson 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
$143 nightly
$168 total
Sep 3 - Sep 4
Total with taxes and fees
9/10 Wonderful! (4,290 reviews)
"Hotel was nice. We had a large king suite. It was nice and clean. Didn’t have much of a view but we were only there for a night. Overall hotel was great. Several bars onsite. And Swizzle was amazing for dinner, views and ambiance! The filet mignon was unreal! I can’t stop talking about it. The only ..."

Reviewed on Aug 24, 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
$172 nightly
$202 total
Aug 27 - Aug 28
Total with taxes and fees
Omni Louisville Hotel
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
$86 nightly
$101 total
Sep 6 - Sep 7
Total with taxes and fees
8.8/10 Excellent! (1,783 reviews)
"Nice stay"

Reviewed on Aug 24, 2026

Holiday Inn Express & Suites Louisville Downtown by IHG
See all 2,128 properties in Jackson
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

$25
per adult
92% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
Kentucky Derby Museum - Admission with Guided Track Visit

Kentucky Derby Museum - Admission with Guided Track Visit

$25
per adult
88% of travellers recommend
Kentucky Derby Museum - Admission with 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
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.