Jackson County Vacations & Trips from $285

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Your Jackson County Vacation

Embark on your next big adventure with a Jackson County vacation package, and leave knowing all the details are already organized. Plus with the ability to tailor your getaway, it'll be one you won't forget. A trip to Jackson County wouldn't be complete without experiencing some of its most renowned cities, starting with Ashland. A couple of the most popular attractions here include Oregon Shakespeare Festival and Lithia Park. Prospect is another favorite city with Jackson County travelers. Visitors to this exciting city enjoy Mill Creek Falls and Joseph H Stewart State Park. Whether you plan to travel for a couple of days or a couple of weeks, Expedia are here to help you organize your next dream Jackson County vacation.

Top destinations in Jackson County

Wonderful camp with lots of places to explore. Taken at the little park. Has a fountain with artificial river/pond you can play in.
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Trail

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The Latest Jackson County Vacation Packages

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

Wine Country Inn

3 out of 5
Price was $378, price is now $285 per person
$285
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
18.8/10 Exceptional! (1,002 reviews)
Cute comfy room. Just needed quick sleep to continue drive. Wish could have explored the town more. Did not try the breakfast but host provided hot water night before for tea. Very gracious hostess. Thanks again.

Reviewed on Nov 14, 2025

Winchester Inn

Winchester Inn

3.5 out of 5
Historic Downtown District
Price was $820, price is now $599 per person
$599
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
19.6/10 Exceptional! (257 reviews)
Beautiful room with comfortable bed. Nice quality bedding.

Reviewed on Oct 26, 2025

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $468, price is now $369 per person
$369
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
19.2/10 Exceptional! (1,003 reviews)
Great Staff, cozy room, comfy bed and pillows. Over looking the pool was a plus. Foid and drinks were top notch.

Reviewed on Nov 20, 2025

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
Price was $408, price is now $322 per person
$322
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
18/10 Exceptional! (1,497 reviews)
Excellent stay. We would go there again.

Reviewed on Nov 22, 2025

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
Price was $491, price is now $394 per person
$394
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
18.4/10 Exceptional! (1,000 reviews)
Front desk staff made me feel welcome and were very helpful!!!

Reviewed on Nov 18, 2025

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Find the Best Jackson County Vacation Packages

Jackson County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rogue Valley Intl. Airport (MFR)
Top Sights
Lithia Park, Howard Prairie Lake and Emigrant Lake
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.