Jackson Vacation Packages
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- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Jackson Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Paintsville
Price was CA $801, price is now CA $765 per person
CA $765
per person
Aug 24 - Aug 27
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Lexington (LEX)
7.6/10 Good! (553 reviews)
The staff was very helpful and friendly. The room was cozy and clean.
Reviewed on Jun 25, 2026
GuestHouse Lexington
Price was CA $802, price is now CA $771 per person
CA $771
per person
Aug 24 - Aug 27
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Lexington (LEX)
8.4/10 Very good! (1,600 reviews)
Clean, comfortable, and very friendly staff. We will definitely plan to stay again when traveling through Lexington!
Reviewed on Jun 29, 2026
Jackson Hotel Deals
Secluded with amazing view from hot tub.Gated mountain top.Won’t be disappointed
Jackson KY
10/10 Exceptional! (360 reviews)
"Everything was just wonderful!"
Reviewed on Jun 27, 2026
Secluded with best views in E. KY. Can see 3 states.You won’t be disappointed!!!
Jackson KY
The price is CA $212 per night from Jul 19 to Jul 20
CA $212
CA $398 total
Jul 19 - Jul 20
includes taxes & fees
10/10 Exceptional! (420 reviews)
"Beautiful view! Quiet, secluded, and very relaxing."
Reviewed on Jun 16, 2026
Sleeps 11, an amazing view. See 3 states on a clear day. Pic don’t do it justice
Jackson KY
9.8/10 Exceptional! (99 reviews)
"Our week-long stay at the cabin was an absolute delight. The breathtaking views from the deck were simply incredible, especially during the sunrises and sunsets. One memorable day, we experienced a storm, and the rhythmic sound of rain hitting the roof, coupled with the moody and cloudy view, created ..."
Reviewed on Jun 20, 2026
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.
