Historic Jacksonville Vacations from $261

Name: Flagship Inn of Ashland
Price range: $83 total
Rating: 8.8

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The Latest Historic Jacksonville vacation packages

Price found within the past 48 hours. Click for updated prices.

Out 'N' About Treehouse Treesort

Save 100% on your flight

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip flight included

Las Vegas (LAS) to Medford (MFR)

9/10 Wonderful! (2 reviews)

Ashland Hills Hotel & Suites

per person

Oct 18 - Oct 22

found 20 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Medford (MFR)

9/10 Wonderful! (1,476 reviews)

Beautiful grounds surrounding the property. Little dissapointed spa is gone but got over that quickly.

Reviewed on Aug 15, 2025

Rogue Regency Inn and Suites

per person

Oct 18 - Oct 22

found 20 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Medford (MFR)

9/10 Wonderful! (2,221 reviews)

Great room- roomt amd quiet. Comfortable bed.

Reviewed on Aug 17, 2025

Wine Country Inn

per person

Sep 19 - Sep 22

found 24 hours ago

Roundtrip non-stop flight included

Las Vegas (LAS) to Medford (MFR)

9.4/10 Exceptional! (1,007 reviews)

Wine country Inn is our favorite place to stay whenever we’re in Jacksonville, Oregon to visit our daughter and grandchildren!

Reviewed on Aug 14, 2025

Ashland Springs Hotel

Historic Downtown District

per person

Sep 19 - Sep 22

found 24 hours ago

Roundtrip non-stop flight included

Las Vegas (LAS) to Medford (MFR)

9.2/10 Wonderful! (1,006 reviews)

The bed was very comfortable and décor was nice. Easy walk to anything downtown. There was a charger box to charge multiple electronics but it only worked intermittently.

Reviewed on Aug 12, 2025

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Discover the most popular places to visit in Historic Jacksonville

One of about a dozen wineries located here along the Applegate Wine Trail.

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.

Art Presence Art Center

Enjoy a show at Art Presence Art Center, a theater with a story to tell in Jacksonville. While you're here, you can savor the top-notch restaurants.

Kharmic Creations

Enjoy an outing to Kharmic Creations during your stay in Jacksonville. Savor the charming coffeehouses and top-notch restaurants while in town.

What to do in Historic Jacksonville

Ashland Puzzling Adventure

$35

per traveler

4 Day Wilderness Raft Trip on the Rogue River

$1,550

per adult

See all activities in Historic Jacksonville

Historic Jacksonville Hotel Deals

Rogue Regency Inn and Suites

2300 Biddle Rd, Medford, OR

Fully refundableReserve now, pay when you stay

$108 nightly

$122 total

Aug 19 - Aug 20

Total includes taxes and fees

8.8/10 Excellent! (2,269 reviews)

"Great room- roomt amd quiet. Comfortable bed."

Reviewed on Aug 17, 2025

Quality Inn & Suites Medford Airport

1950 Biddle Rd, Medford, OR

Fully refundableReserve now, pay when you stay

$81 nightly

$91 total

Sep 8 - Sep 9

Total includes taxes and fees

8.4/10 Very Good! (1,007 reviews)

"Clean room, bad water and water pressure, nice service"

Reviewed on Aug 16, 2025

Flagship Inn of Ashland

1193 Siskiyou Blvd, Ashland, OR

Fully refundableReserve now, pay when you stay

$74 nightly

$83 total

Sep 2 - Sep 3

Total includes taxes and fees

8.8/10 Excellent! (1,006 reviews)

"Friendly and helpful staff. Excellent value for comfortable stay!"

Reviewed on Aug 15, 2025

See all 670 properties in Historic Jacksonville

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.