Jackson County Vacations & Trips from $549

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Your Jackson County Vacation

Choose a vacation package to Jackson County and make planning your getaway a breeze. With all the details arranged before you depart, you can focus on enjoying every moment in this amazing destination. Wondering where to stay during your trip to Jackson County? Freetown is a leading city you won't want to miss. From the instant you book your Jackson County vacation to when you return home, Expedia has you covered every step of the way.

Top destinations in Jackson County

A snow-covered mountain with a clear sky and a sunset.

Seymour

Seymour
A courthouse with a clock tower, surrounded by trees and a parking lot.

Brownstown

Brownstown

The Latest Jackson County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

Shively
$549
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.6/10 Excellent! (1,003 reviews)
Friendly staff, clean lobby and room was big and comfortable.

Reviewed on Oct 2, 2026

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

Fairgrounds
$661
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.8/10 Excellent! (1,859 reviews)
Excellent staff and service, Love having a restaurant in house, especially with none located nearby.

Reviewed on Oct 2, 2026

The Grady

The Grady

Downtown Louisville
$634
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9.4/10 Exceptional! (1,011 reviews)
Great place to stay in downtown Louisville. Staff is always friendly and helpful.

Reviewed on Oct 2, 2026

The Brown Hotel

The Brown Hotel

Downtown Louisville
$567
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9.4/10 Exceptional! (1,333 reviews)
Hyatt Regency Louisville

Hyatt Regency Louisville

Downtown Louisville
$572
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
Gorgeous atrium style hotel just steps away from convention center. Lots to do and see near hotel.

Reviewed on Oct 1, 2026

Find the Best Jackson County Vacation Packages

Jackson County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Indianapolis Intl. Airport (IND)

Jackson County Hotel Deals

Quality Inn Seymour I-65

Quality Inn Seymour I-65

2075 E Tipton St Seymour IN
Fully refundable
$81 nightly
$90 total
Nov 2 - Nov 3
Total with taxes and fees
7/10 Good! (646 reviews)
"Comfortable beds and good ac."

Reviewed on Oct 1, 2026

Quality Inn Seymour I-65
Hilton Garden Inn Bloomington

Hilton Garden Inn Bloomington

245 North College Avenue Bloomington IN
Fully refundableReserve now, pay when you stay
$118 nightly
$132 total
Oct 11 - Oct 12
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Great room. Very clean. New !"

Reviewed on Oct 1, 2026

Hilton Garden Inn Bloomington
Postcard Cabins Brown County Indiana, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Brown County Indiana, Outdoor Collection by Marriott Bonvoy

6249 Poplar Grove Rd Columbus IN
$150 nightly
$173 total
Nov 2 - Nov 3
Total with taxes and fees
Postcard Cabins Brown County Indiana, Outdoor Collection by Marriott Bonvoy
See all 881 properties in Jackson County
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.

Stay near popular Jackson County attractions

A gravel road flanked by tall grasses and a large tree.
Photo by Susan Ross

Muscatatuck National Wildlife Refuge

8.8/10 (28 reviews)
You can take time to visit Muscatatuck National Wildlife Refuge during your travels to Seymour. While you're in the area, wander around the natural setting.
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An aerial view of a golf course with sand bunkers, a pond, and surrounding residential buildings.

Seymour Golf Course

Enjoy a round of golf in Seymour at Seymour Golf Course. While in this family-friendly area, you can enjoy the restaurants.
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Southern Indiana Center for the Arts

6.0/10 (1 review)
Enjoy an outing to Southern Indiana Center for the Arts during your stay in Seymour. You can enjoy the coffeehouses while in the area.
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Peters Lake

Commune with nature and explore the great outdoors at Peters Lake during your travels in Seymour. While in this family-friendly area, you can enjoy the restaurants.
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Cypress Lake

Commune with nature and explore the great outdoors at Cypress Lake during your travels in Seymour. While in this family-friendly area, you can enjoy the restaurants.
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Shields Park

Explore the great outdoors at Shields Park, a lovely green space in Seymour. While in this family-friendly area, you can enjoy the restaurants.
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Shoppes at Seymour

You can enjoy retail therapy at Shoppes at Seymour during your visit to Seymour. While in this family-friendly area, you can enjoy the restaurants.
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Sharps Woods

Explore the great outdoors at Sharps Woods, a lovely green space in Seymour. While in this family-friendly area, you can enjoy the restaurants.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.