Jackson Vacations from $483

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The Latest Jackson vacation packages

Price found within the past 48 hours. Click for updated prices.
Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was $545, price is now $483 per person
$483
per person
Feb 27 - Mar 2
found 9 hours ago
Roundtrip flight included
Dallas (DAL) to Lexington (LEX)
8.2/10 Very Good! (1,040 reviews)
Nice location, staff is nice. Had iss with dog barking one night but staff moved us to new room.

Reviewed on Jan 17, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $1,178, price is now $949 per person
$949
per person
Apr 10 - Apr 13
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Lexington (LEX)
8.8/10 Excellent! (1,002 reviews)
Great hotel in great location. Clean, modern, and artsy. Room was very comfortable and the shower was great, which is big for me. It had good water pressure with hot water. Check in and out was quick and easy.

Reviewed on Jan 20, 2026

Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $1,049, price is now $896 per person
$896
per person
Apr 23 - Apr 26
found 8 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Lexington (LEX)
9.4/10 Exceptional! (1,003 reviews)
very nicely decorated & very clean. test that always tells the most is what your socks look like after walking around the carpet lol & I can say, they were still white. staff was also super nice and helpful. burger at the restaurant downstairs was phenomenal. only downside of my stay is that I need to sleep in a cold room & for some reason I couldn’t get my air or the fan on the unit to stay on. they say you can’t set it lower than 68° which was fine. but I really need air flow/fan to sleep & it wouldn’t set the fan to on. besides that, great stay.

Reviewed on Jan 25, 2026

The Manchester

The Manchester

4 out of 5
Distillery District
Price was $1,262, price is now $1,106 per person
$1,106
per person
Apr 23 - Apr 26
found 8 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Lexington (LEX)
9.6/10 Exceptional! (1,046 reviews)
Great place to stay, eat and drink.

Reviewed on Jan 20, 2026

The Sire Hotel Lexington, Tapestry Collection by Hilton

The Sire Hotel Lexington, Tapestry Collection by Hilton

3.5 out of 5
Downtown Lexington
Price was $1,019, price is now $899 per person
$899
per person
Apr 23 - Apr 26
found 8 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Lexington (LEX)
9.4/10 Exceptional! (838 reviews)
Personable staff. Clean rooms. Easy parking. Large rooms.

Reviewed on Jan 8, 2026

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Jackson Hotel Deals

Secluded with amazing view from hot tub.Gated mountain top.Won’t be disappointed

Secluded with amazing view from hot tub.Gated mountain top.Won’t be disappointed

Jackson KY
$194 nightly
The price is $207 total per night from Jan 28 to Jan 29
$207 total
Jan 28 - Jan 29
Total with taxes and fees
10/10 Exceptional! (326 reviews)
Amazing!

Reviewed on Jan 19, 2026

Secluded with amazing view from hot tub.Gated mountain top.Won’t be disappointed
Secluded with best views in E. KY. Can see 3 states.You won’t be disappointed!!!

Secluded with best views in E. KY. Can see 3 states.You won’t be disappointed!!!

Jackson KY
$197 nightly
The price is $211 total per night from Jan 28 to Jan 29
$211 total
Jan 28 - Jan 29
Total with taxes and fees
10/10 Exceptional! (405 reviews)
Cabin was perfect for a small minimalist get away. Clean and has a pretty view.

Reviewed on Jan 12, 2026

Secluded with best views in E. KY. Can see 3 states.You won’t be disappointed!!!
Secluded with amazing view

Secluded with amazing view

2 out of 5
Jackson KY
10/10 Exceptional! (3 reviews)
We had an amazing stay at this beautiful mountain cabin. The location was peaceful and surrounded by beautiful scenery, making it the perfect place to relax and unplug. The cabin itself was clean, cozy, and well-equipped with everything we needed and in excellent condition. We especially loved the ...

Reviewed on Jan 3, 2026

Get rates
Secluded with amazing view
See all 676 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.

Find the Best Jackson Vacation Packages

Jackson Essential Information

Language
English
Currency
U.S dollars
Population
2,200
Max Temp Winter
45ºF
Max Temp Summer
85ºF

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Frequently asked questions

How much does a Jackson vacation package cost?
Offering excellent value package deals from $483 on Expedia, you'll be surprised at how little a vacation to Jackson costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Jackson?
November, December and January are great times to look for cheap Jackson vacation packages. Traveling in quieter months means you can generally find lower prices on accommodations and flights.
How many days is enough for Jackson?
Typically, a handful of days is enough to visit the major attractions during your Jackson vacation. However, if you'd like to have time to kick back or go on day tours, think about extending your itinerary.
How to find the best Jackson package deals?
Use Expedia's filters to help you find some of the best Jackson package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Jackson package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Jackson vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays separately. Better still, you can customize your Jackson getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Jackson?
Secure amazing discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Jackson trip.
Does Expedia offer Book Now, Pay Later Jackson vacation packages?
Your Jackson break is meant to be a relaxing escape from your busy life, not a source of money-related stress. So to give you a little more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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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.