A brick building labeled "City Hall" with a white door and windows, a bench outside, and a tree nearby.
Photo by Shannon Willitts
Open Photo by Shannon Willitts

Jacksonville Historic District Vacations from $361

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The Latest Jacksonville Historic District Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A sign for Prospero's Flagship Inn with a star emblem and a pedestrian crossing sign nearby.
    Jan 8 - Jan 10

    Prospero's Flagship Inn + Flight

    Ashland
    2 nights
    2.5 star property
    8.4/10 - Very good (1,495 reviews)
    Roundtrip • Phoenix (PHX) - Medford (MFR)
    PHX - MFR • 1 stop MFR - PHX • 1 stop
    $398
    $361
    per traveler
    found 1 day ago
    Prospero's Flagship Inn
  • A large, white, multi-story house with a stone foundation, multiple chimneys, and a well-maintained lawn.
    Jan 8 - Jan 10

    Hummingbird Estate Wine & Suites + Flight

    Central Point
    2 nights
    4.5 star property
    9.6/10 - Exceptional (199 reviews)
    "Amazing room, wonderful staff, wines were excellent. Will be visiting again!"
    Reviewed October 27, 2026
    Roundtrip • Phoenix (PHX) - Medford (MFR)
    PHX - MFR • 1 stop MFR - PHX • 1 stop
    $480
    $421
    per traveler
    found 1 day ago
    Hummingbird Estate Wine & Suites
  • A large, two-story house with a wrap-around porch and a steeply pitched roof.
    Jan 8 - Jan 10

    Winchester Inn + Flight

    Historic Downtown District
    2 nights
    3.5 star property
    9.6/10 - Exceptional (292 reviews)
    "Well maintained and beautiful Victorian boutique hotel located within a short walk to Main Street. Our room had all the modern amenities. Staff very helpful. Breakfast was good."
    Reviewed November 10, 2026
    Roundtrip • Phoenix (PHX) - Medford (MFR)
    PHX - MFR • 1 stop MFR - PHX • 1 stop
    $515
    $467
    per traveler
    found 1 day ago
    Winchester Inn
  • A deck with a fire pit, outdoor seating, and a view of the countryside.
    Jan 8 - Jan 10

    Grandview of Ashland + Flight

    Ashland
    2 nights
    3.0 star property
    10/10 - Exceptional (11 reviews)
    "This property was absolutely magic! The home is incredibly beautiful and welcoming. The property owners were incredibly easy to communicate with and we felt like we were at a resort. The surroundings are stunning and while you feel completely removed from everything you are just minutes from OSF in Ashland. From drinking coffee while watching deer in the yard to just taking in the panoramic gorgeous views, we didn't want to leave the house. I honestly can not wait to use it again!"
    Reviewed October 11, 2026
    Roundtrip • Phoenix (PHX) - Medford (MFR)
    PHX - MFR • 1 stop MFR - PHX • 1 stop
    $736
    $669
    per traveler
    found 1 day ago
    Grandview of Ashland
  • A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.
    Jan 8 - Jan 10

    Savage Upon Siskiyou + Flight

    Siskiyou-Hargadine Historic District
    2 nights
    3.0 star property
    10/10 - Exceptional (2 reviews)
    "Had an amazing stay, thank you!"
    Reviewed August 5, 2026
    Roundtrip • Phoenix (PHX) - Medford (MFR)
    PHX - MFR • 1 stop MFR - PHX • 1 stop
    $661
    $605
    per traveler
    found 1 day ago
    Savage Upon Siskiyou

Discover the most popular places to visit in Jacksonville Historic District

Beekman House

10.0/10 (1 review)
You can browse the exhibits at Beekman House, a museum with a storied past, during your trip to Jacksonville. While you're here, you can savor the top-notch restaurants.
See properties

Jacksonville Historic District Hotel Deals

An outdoor patio with seating under a pergola, string lights, and a fire pit.

Magnolia Hotel

Magnolia Hotel
3.0 star property
Jacksonville Historic District
9.6 out of 10, Exceptional, (805 reviews)
$158 nightly
The price is $175
Nov 13 - Nov 14
Total with taxes and fees
Magnolia Hotel
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 Jacksonville Historic District
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.