Jackson County Vacations & Trips from $546
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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
Trail
The Latest Jackson County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Ashland Hills Hotel & Suites
Price was $652, price is now $546 per person
$546
per person
Jan 1 - Jan 5
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Medford (MFR)
9/10 Wonderful! (1,497 reviews)
Clean hotel perfect stop over with our dog. We had a sliding glass door onto a courtyard great for letting our dog out to the bathroom. Luna restaurant was tasty fish and chips. Nice to sit by the fire place.
Reviewed on Nov 24, 2025
Winchester Inn
Historic Downtown District
Price was $786, price is now $595 per person
$595
per person
Jan 1 - Jan 5
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Medford (MFR)
9.8/10 Exceptional! (257 reviews)
Beautiful room with comfortable bed. Nice quality bedding.
Reviewed on Oct 26, 2025
Compass by Margaritaville in Medford
Price was $750, price is now $622 per person
$622
per person
Jan 1 - Jan 5
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Medford (MFR)
9.6/10 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 Springs Hotel
Historic Downtown District
Price was $789, price is now $661 per person
$661
per person
Jan 1 - Jan 5
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Medford (MFR)
9.2/10 Wonderful! (1,000 reviews)
Nice room. Need to update electrical in room. Could not plug blow dryer in bathroom, the outlet did not work properly. The power strip located on desk was worn and when I plugged by phone charger in it, it constantly fell out. I went to front desk an requested they change the power strip. A maintenance person was at the desk as well and said would change it. It was never done.
Reviewed on Nov 24, 2025
McCall House Boutique Inn
Historic Downtown District
Price was $804, price is now $676 per person
$676
per person
Jan 1 - Jan 5
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Medford (MFR)
9.2/10 Wonderful! (574 reviews)
The room and the breakfast. The staff were very nice.
Reviewed on Nov 23, 2025
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 |
Jackson County Hotel Deals
Rogue Regency Inn and Suites
2300 Biddle Rd Medford OR
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $106 total per night from Nov 30 to Dec 1
$106 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (2,630 reviews)
Quite nice, will come again!
Reviewed on Nov 23, 2025
Flagship Inn of Ashland
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $81 total per night from Dec 26 to Dec 27
$81 total
Dec 26 - Dec 27
Total with taxes and fees
8.6/10 Excellent! (1,174 reviews)
The room was fine and the staff help with the reservation was excellent. The problem was that I thought I had made a reservation for Nov. 23 and 24, but it was instead made for Nov. 24 and 25. Staff at the motel fixed this. I don't know how this happened, but will be sure to read the small print ...
Reviewed on Nov 26, 2025
My Place Hotel-Medford OR
580 Airport Rd Medford OR
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $108 total per night from Dec 11 to Dec 12
$108 total
Dec 11 - Dec 12
Total with taxes and fees
9/10 Wonderful! (1,516 reviews)
The stay was good overall. Room was clean.
Reviewed on Nov 27, 2025
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.
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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.
