Jacksonville Historic District Vacations from $569
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The Latest Jacksonville Historic District Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Wine Country Inn
Price was $694, price is now $569 per person
$569
per person
May 7 - May 11
found 18 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Medford (MFR)
9.4/10 Exceptional! (1,005 reviews)
Parking lot appeared to be safe. Breakfast items were limited, but enough to satisfy our needs.
Reviewed on Mar 29, 2026
Hummingbird Estate Wine & Suites
Price was $872, price is now $659 per person
$659
per person
May 7 - May 11
found 18 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Medford (MFR)
9.6/10 Exceptional! (156 reviews)
Charming vintage winery with great history and lovely rooms. The Syrah suite was clean and comfortable. The sunrise in the morning was spectacular. The tasting room is directly below the suite and can be loud but closes around 7 during the week. I don’t think I would stay here during an event unless I was participating in the event. So check the calendar first if noise is an issue for you. The grounds are wonderful and there are many spots to sit and enjoy. At night the terrace is lovely with the fires going. We played a bit of pickleball as well. Highly recommend with the caveat of checking for events first if noise is an issue for you.
Reviewed on Feb 28, 2026
Jacksonville Historic District Hotel Deals
Magnolia Hotel
245 North 5th Street Jacksonville OR
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $170 total per night from Apr 3 to Apr 4
$170 total
Apr 3 - Apr 4
Total with taxes and fees
9/10 Wonderful! (780 reviews)
Very comfortable and quiet. We felt well provided for and we left quite content.
Reviewed on Mar 22, 2026
TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO BRITT FESTIVAL
Jacksonville OR
$309 nightly
The price is $341 total per night from Apr 19 to Apr 20
$341 total
Apr 19 - Apr 20
Total with taxes and fees
10/10 Exceptional! (37 reviews)
Super great space! Cute, cozy, and easy walk to downtown and the Britt. Perfect girls getaway!
Reviewed on Aug 14, 2025
Stratford Inn
555 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Apr 5 to Apr 6
$123 total
Apr 5 - Apr 6
Total with taxes and fees
9.4/10 Exceptional! (1,734 reviews)
Great location. Clean and spacious room.
Reviewed on Mar 31, 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.
Discover the most popular places to visit in Jacksonville Historic District
Applegate Lake
Commune with nature and explore the great outdoors at Applegate Lake during your travels in Jacksonville. Discover the restaurants and live music in this walkable area.
Red Lily Vineyards
You can enjoy a tasting or tour at Red Lily Vineyards during your travels to Jacksonville. Discover the coffeehouses and festivals in this walkable area.
Beekman House
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.
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- Jacksonville Vacations
- Beekman House
- Sarah Zigler Interpretive Trail
- Britt Pavilion
- Visit Jacksonville
- Blackbird Statue
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- Alba Park
- Medford City Hall
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- Medford Central Library
- Fichtner-Mainwaring Park
- Rogue Valley Mall
- Medford Railroad Park
- Southern Oregon University Medford Campus
- Visit Medford
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.