The Best Winery Hotels in Jacksonville Historic District, OR from ₩253,756 in 2026

The towns theme of swags of incense Pine makes for a festive holiday town to put on your itinerary.

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Check availability on Jacksonville Historic District Winery Hotels

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Our top choices for Jacksonville Historic District hotels with winery

Cottage Nine in Jacksonville

Jacksonville Historic District

₩369,122 total

includes taxes & fees

Mar 18 - Mar 19

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Top Jacksonville Historic District Hotel Reviews

Flagship Inn of Ashland

10/10 Excellent

"Lovely spot!!"

Super 8 by Wyndham Central Pt Medford

4/10 Poor

"Things were falling apart. The room I was assigned smelled like a kennel. I had to hook up the toilet to even make it so it could even flush, the shower was dangerously slippery with no grip pads. The pool water was pretty off on its color and dingy. The food area though they provided stuff was too packed in and limited in space with very small options and most of them exhausted before even 9am "