Jackson Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top Jackson Vacation Deals

Price found within the past 48 hours. Click for updated prices.
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was CA $1,164, price is now CA $969 per person
CA $969
per person
Aug 26 - Aug 31
just found
Roundtrip flight included
Toronto (YTO) to Lexington (LEX)
8.8/10 Excellent! (1,001 reviews)
Stayed here many times and have been pleased. Yet now, the restaurant closed for renovations and there are no accommodations for breakfast or most importantly coffee on Mondays and Tuesdays. If I'd known, I would've stayed elsewhere.

Reviewed on Jul 14, 2026

Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was CA $1,203, price is now CA $1,071 per person
CA $1,071
per person
Aug 26 - Aug 31
just found
Roundtrip flight included
Toronto (YTO) to Lexington (LEX)
8/10 Very good! (1,057 reviews)

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was CA $1,247, price is now CA $1,114 per person
CA $1,114
per person
Aug 26 - Aug 31
just found
Roundtrip flight included
Toronto (YTO) to Lexington (LEX)
9.4/10 Exceptional! (1,005 reviews)

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
Price was CA $1,094, price is now CA $981 per person
CA $981
per person
Aug 26 - Aug 31
just found
Roundtrip flight included
Toronto (YTO) to Lexington (LEX)
8.8/10 Excellent! (1,004 reviews)
Unfortunately, the airport shuttle driver had left early on the day that I arrived however, they said I could Uber and they would reimburse me which I felt was a reasonable response.

Reviewed on Jul 16, 2026

Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was CA $1,095, price is now CA $1,002 per person
CA $1,002
per person
Aug 26 - Aug 31
just found
Roundtrip flight included
Toronto (YTO) to Lexington (LEX)
9.4/10 Exceptional! (1,103 reviews)
Great hotel! Clean, good location, restaurant and bar options, great staff

Reviewed on Jul 14, 2026

Ready to book your vacation to Jackson?

 

Choose your dates

Jackson Hotel Deals

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
The price is CA $176 per night from Aug 3 to Aug 4
CA $176
CA $352 total
Aug 3 - Aug 4
includes taxes & fees
10/10 Exceptional! (425 reviews)
"Amazing property! Secluded, peaceful and quite. Just you and nature. The views from the hot tub are unreal! Definitely will be back again!"

Reviewed on Jul 11, 2026

Secluded with best views in E. KY. Can see 3 states.You won’t be disappointed!!!
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
The price is CA $160 per night from Aug 3 to Aug 4
CA $160
CA $322 total
Aug 3 - Aug 4
includes taxes & fees
10/10 Exceptional! (364 reviews)
"Great stay! Property was amazing!"

Reviewed on Jul 10, 2026

Secluded with amazing view from hot tub.Gated mountain top.Won’t be disappointed
Sleeps 11, an amazing view. See 3 states on a clear day. Pic don’t do it justice

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

Jackson KY
9.8/10 Exceptional! (100 reviews)
"10/10 highly recommend staying here!"

Reviewed on Jul 5, 2026

Get rates
Sleeps 11, an amazing view. See 3 states on a clear day. Pic don’t do it justice
See all 724 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Jackson vacation package cost?
Offering great value package deals from CA $969 on Expedia, you'll be thrilled with how little a vacation to Jackson costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Jackson?
Travel in the off-peak season and you're likely to find cheap Jackson vacation packages. Remember that public holidays and major festivals and events can have an impact on prices, so do some research before you go.
How many days is enough for Jackson?
The ideal length of your Jackson vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to visit all the top sights and discover some hidden treasures along the way.
How to find the best Jackson package deals?
Landing a cheap Jackson package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most affordable Jackson package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Jackson vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component individually. And you'll still have the freedom to create a customized Jackson vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Jackson?
If you're planning a spur-of-the-moment Jackson adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Jackson?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Jackson.
  2. Budget wisely: In addition to the price of your stay, you should consider other expenses too. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that may arise during your trip to Jackson.
  3. Decide your trip length: Think about how long you'd like to spend exploring Jackson. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Jackson vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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