Jackson County Vacations & Trips from $432
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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.
The Latest Jackson County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Louisville Airport
Fairgrounds
Price was $563, price is now $432 per person
$432
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,001 reviews)
Nice spacious rooms with comfy beds. Not a lot of food options for breakfast
Reviewed on Aug 10, 2025
Galt House Hotel Trademark Collection by Wyndham
Downtown Louisville
Price was $978, price is now $696 per person
$696
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (3,563 reviews)
Property is great, parking garage of course spendy. The area around accessing the elevators from the garage below to the property reaks of urine! To the point you want to wash your shoes off after!
Reviewed on Sep 9, 2025
Hilton Garden Inn Louisville/Northeast
Price was $620, price is now $461 per person
$461
per person
Oct 30 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Louisville (SDF)
9/10 Wonderful! (172 reviews)
Very nice property with easy access off expressway. If staying here ask for a room at the front of the building. Our room was in the back and traffic noise from highway was disturbing while trying to sleep. Staff was very friendly and property was clean.
Reviewed on Aug 26, 2025
Pillow and Paddock B&B
Price was $663, price is now $510 per person
$510
per person
Oct 21 - Oct 24
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)
10/10 Exceptional! (50 reviews)
This has been our second time staying here and we will continue to come back. Beautiful home, amazing breakfasts, and wonderful hosts, not much else we could ask for.
Reviewed on Apr 27, 2025
Jackson County Hotel Deals
Biddle Hotel and Conference Center
900 E. 7th St., Bloomington, IN
$139 nightly
The price is $156 total per night from Sep 11 to Sep 12
$156 total
Sep 11 - Sep 12
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Bloomington
3380 W Runklel Way, Bloomington, IN
$94 nightly
The price is $105 total per night from Sep 28 to Sep 29
$105 total
Sep 28 - Sep 29
Total with taxes and fees
Cascades Inn
2601 N Walnut Street, Bloomington, IN
$72 nightly
The price is $80 total per night from Sep 10 to Sep 11
$80 total
Sep 10 - Sep 11
Total with taxes and fees
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.
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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.