Jackson Vacation Packages 2026 from $487

Jackson flight + hotel vacation packages

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

Baymont by Wyndham Winchester

$487

per person

Jul 27 - Jul 31

found 3 hours ago

Roundtrip flight included

New York (NYC) to Lexington (LEX)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Guests will appreciate freebies like continental breakfast and free self parking.

Comfort Inn & Suites Mount Sterling

$555

per person

Jul 27 - Jul 31

found 3 hours ago

Roundtrip flight included

New York (NYC) to Lexington (LEX)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's an indoor pool on site, and a 24-hour front desk and express check-in are also provided.

Holiday Inn Express & Suites Mt Sterling North by IHG

$620

per person

Jul 27 - Jul 31

found 3 hours ago

Roundtrip flight included

New York (NYC) to Lexington (LEX)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

21c Museum Hotel Lexington

Downtown Lexington

$1,191

per person

Jul 27 - Jul 31

found 2 hours ago

Roundtrip flight included

New York (NYC) to Lexington (LEX)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a 24-hour business center, and a snack bar/deli are also offered.

Montgomery Inn BnB

$492

per person

Jun 18 - Jun 21

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Lexington (LEX)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A terrace, a garden, and a lobby fireplace are also on offer.

Top Jackson hotels deals

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

Jackson KY

$259 nightly

$277 total

Jun 4 - Jun 5

Total with taxes and fees

A hot tub is featured at this cabin, along with barbecue grills.

Hot Tub

Kitchen

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

Jackson KY

$209 nightly

$224 total

May 27 - May 28

Total with taxes and fees

A hot tub is featured at this cabin, along with barbecue grills.

Hot Tub

Kitchen

Sleeps 11, an amazing view. See 3 states on a clear day. Pic don’t do it justice

Jackson KY

Get rates

A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.

Hot Tub

Kitchen

Secluded with amazing view

Jackson KY

Get rates

This cabin features a gym and a hot tub. Laundry facilities and barbecue grills are also provided.

Hot Tub

Kitchen

Natural Bridge State Resort Park

2135 Natural Bridge Road Slade KY

$121 nightly

$133 total

Jun 14 - Jun 15

Total with taxes and fees

This cabin features a restaurant, a seasonal outdoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A picnic area is provided and the front desk is staffed around-the-clock.

Pool

Breakfast included

Black Bear Lodge Motel

781 Natural Bridge Rd Slade KY

$88 nightly

$97 total

May 27 - May 28

Total with taxes and fees

This motel features a coffee shop, barbecue grills, and free self parking. A convenience store and a picnic area are also provided.

Parking included

Air conditioning

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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 are vacation packages to Jackson?

Treat yourself to a memorable travel experience in Jackson with a vacation package starting from just $487. Booking your flights and hotels with Travelocity is easy. What's more, our package deals will leave you with more cash in your pocket for fun times.

How long should my Jackson vacation be?

Usually, 4 nights is how long the majority of travelers spend checking out Jackson. Wondering whether that'll be enough time to fit in everything on your bucket list? Stay a couple more nights so you don't miss a thing.

Where can I get the best vacation package deals for Jackson?

It's hard to look past Travelocity when it comes to putting together your Jackson package deal. There are as many as 400 airlines and 1,000,000 worldwide properties to choose from. Book your trip now and get ready to tick another exciting place off your travel bucket list.

Why should I purchase my Jackson vacation package via Travelocity?

We have a destination for every type of traveler, top-quality service and customer support available 24/7. In addition to that, we'll match any better price you discover with our Price Match Guarantee.

Will I save money on my Jackson car rental if I book it with a hotel or flight?

With a Jackson vacation package, you can bundle your hotel, car and flight bookings and save a ton. If you're in the mood to explore the best of this exciting region, why not head to Dollywood? This renowned attraction is 120 mi from Jackson. With a rental car, you'll be there before you know it.

Where should I stay when visiting Jackson?

The Best views in the area. See 3 states on a clear day. Pics don't do it Justice. is popular with many visitors. Book now to avoid missing out.