Jackson Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Jackson Vacation Packages

Jackson Hotel Deals

Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road, Slade, KY
Fully refundableReserve now, pay when you stay
The price is ₩133,172 per night from Sep 1 to Sep 2
₩133,172
₩146,803 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,666 reviews)
"We loved the location and the staff. Breakfast was super. The room could use a refresh… especially the bathroom caulk and the doors throughout. The entire place had a slight musty odor."

Reviewed on Aug 18, 2025

Natural Bridge State Resort Park
Black Bear Lodge Motel

Black Bear Lodge Motel

2.5 out of 5
781 Natural Bridge Rd, Slade, KY
The price is ₩122,906 per night from Aug 24 to Aug 25
₩122,906
₩135,490 total
Aug 24 - Aug 25
includes taxes & fees
8/10 Very Good! (586 reviews)
"Nice accommodations. 👍👍"

Reviewed on Aug 17, 2025

Black Bear Lodge Motel
Comfort Suites Prestonsburg West

Comfort Suites Prestonsburg West

2.5 out of 5
51 Hal Rogers Dr, Prestonsburg, KY
Fully refundableReserve now, pay when you stay
The price is ₩153,744 per night from Aug 24 to Aug 25
₩153,744
₩174,378 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (649 reviews)
"The beds were very comfortable and the couch was too. Breakfast was fabulous! Would definitely stay there again."

Reviewed on Aug 13, 2025

Comfort Suites Prestonsburg West
See all 640 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.

Frequently asked questions

How much does a Jackson vacation package cost?
Offering excellent value package deals 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?
To score cheap Jackson vacation packages, organize your trip outside of peak times like public holidays and major events. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Jackson?
The ideal length for your Jackson vacation depends on what you'd like to see. Generally, a few days to a week will give you enough time to tick off all the major sights and discover some hidden spots along the way.
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.
How to plan a trip to Jackson?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Jackson.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to put aside for your trip to Jackson. Then, select a property that fits your budget, whether that's an affordable option or a deluxe getaway.
  3. Set the duration of your trip: Start by listing all the activities and sights you'd like to experience in Jackson. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Jackson vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.