Kentucky Bend Vacations from $232

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

The Latest Kentucky Bend Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A spacious room with a wooden floor, a sofa, a desk, and various potted plants.
    Dec 30 - Jan 5

    Ole South Inn Jackson I 40 TN + Flight

    Denmark
    6 nights
    2.5 star property
    5.6/10 - (21 reviews)
    "I can’t explain in my words how people can go have a rest here. This place was the worst nightmare for me as soon as I entered the room all the bugs and insects were on the wall , curtain, and bed. Bedsheets all dusty, my god can’t imagine so I had to get back from there and I rather feel okay to sleep inside my own car. I understand the budget is friendly, but it doesn’t mean there should be a lack of cleanliness . For me, the worst experience to be honest."
    Reviewed October 27, 2026
    Roundtrip • Chicago (ORD) - Memphis (MEM)
    ORD - MEM • Nonstop MEM - ORD • Nonstop
    $306
    $232
    per traveler
    found 1 day ago
    Ole South Inn Jackson I 40 TN
  • A wooden barn-style door leading to a bathroom with a glass shower enclosure.
    Dec 30 - Jan 5

    Magnolia Manor and Chapel + Flight

    Humboldt
    6 nights
    4.0 star property
    10/10 - Exceptional (68 reviews)
    "The speak easy bar. Had a awesome chocolate Old Fasioned and the Memphis Hot chicken with potato salad. Wish we could have stayed longer."
    Reviewed November 7, 2026
    Roundtrip • Chicago (ORD) - Memphis (MEM)
    ORD - MEM • Nonstop MEM - ORD • Nonstop
    $773
    $497
    per traveler
    found 1 day ago
    Magnolia Manor and Chapel
  • A hotel lobby with a wooden floor, a reception desk, a wall-mounted clock, and a framed picture.
    Dec 30 - Jan 5

    Jackson Hotel & Convention Center + Flight

    Jackson
    6 nights
    2.0 star property
    5.6/10 - (999 reviews)
    "The property has gone down since renovations. Floors are not better looking. Plus they stopped breakfast buffet which was good"
    Reviewed November 10, 2026
    Roundtrip • Chicago (ORD) - Memphis (MEM)
    ORD - MEM • Nonstop MEM - ORD • Nonstop
    $357
    $257
    per traveler
    found 1 day ago
    Jackson Hotel & Convention Center
  • A living room with a stone fireplace, a sofa, a red armchair, and a bookshelf.
    Dec 30 - Jan 5

    Country Inn & Suites by Radisson, Jackson, TN + Flight

    Jackson
    6 nights
    3.0 star property
    8.0/10 - Very good (789 reviews)
    "The room was very clean. The staff was very helpful and I will recommend this hotel to my friends/family."
    Reviewed November 3, 2026
    Roundtrip • Chicago (ORD) - Memphis (MEM)
    ORD - MEM • Nonstop MEM - ORD • Nonstop
    $490
    $367
    per traveler
    found 1 day ago
    Country Inn & Suites by Radisson, Jackson, TN
  • A solar-powered charging station with a screen advertising Eos Charge, surrounded by greenery and a residential area.
    Dec 30 - Jan 5

    Red Roof Inn & Suites Jackson, TN + Flight

    Jackson
    6 nights
    2.0 star property
    6.6/10 - (931 reviews)
    Roundtrip • Chicago (ORD) - Memphis (MEM)
    ORD - MEM • Nonstop MEM - ORD • Nonstop
    $344
    $267
    per traveler
    found 1 day ago
    Red Roof Inn & Suites Jackson, TN

Kentucky Bend Hotel Deals

A modern kitchen with a stone backsplash, a dining area with red chairs, and a red accent wall with a framed picture.

Super 8 By Wyndham Marston

Super 8 By Wyndham Marston
2.0 star property
4.9 mi from Kentucky Bend
8.0 out of 10, Very good, (82 reviews)
"The property is pretty tired and needs to be freshened up. Breakfast was pretty minimal and poor quality. Room price was very good, I would call it good basic shelter for 1 night or so."
$58 nightly
The price is $66
Nov 15 - Nov 16
Total with taxes and fees
Super 8 By Wyndham Marston
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.
See all properties in Kentucky Bend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.