Southern Oregon Vacations from $724
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Your Southern Oregon Vacation
With a Southern Oregon vacation package, you can forget about the stress of planning and focus on experiencing what this exciting destination has to offer. A trip to Southern Oregon wouldn't be complete without getting to some of its most well-known cities, starting with Medford. Two of the top attractions here include Britt Pavilion and Lithia & Driveway Fields. Grants Pass should also be on the itineraries of all Southern Oregon travelers. Visitors to this exciting destination enjoy Rogue River and Grants Pass and Josephine County Chamber of Commerce. If you're ready to stop dreaming and start packing, Expedia will help turn your Southern Oregon vacation into a reality.
The Latest Southern Oregon vacation packages
Price found within the past 48 hours. Click for updated prices.
Wine Country Inn
Price was $905, price is now $724 per person
$724
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Medford (MFR)
9.4/10 Exceptional! (1,005 reviews)
Wonderful stay! I loved the grounds and the room was immaculate. The coffee at the front desk was fabulous, too!
Reviewed on May 5, 2026
Hummingbird Estate Wine & Suites
Price was $1,023, price is now $810 per person
$810
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Medford (MFR)
9.6/10 Exceptional! (157 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
Barclay Klum House by WanderLodges
Price was $1,795, price is now $1,426 per person
$1,426
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Medford (MFR)
10/10 Exceptional! (8 reviews)
Excellent location for in Ashland Easy acces to all local areas and the beds were comfortable! Kitchen stocked with all dishes need to cook meals.
Reviewed on Mar 10, 2026
Don't see what you're looking for?
See all available trips from Columbus to Southern Oregon
View all tripsWhere to stay in Southern Oregon
Find the best Southern Oregon areas and neighborhoods for the activities you enjoy most. Learn more about Southern Oregon
Historic Downtown District
1 out of top 10 points of interest in this area
5/5(137 area reviews)
If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Angus Bowmer Theatre are top sights worth seeing.
Discover the most popular places to visit in Southern Oregon
Crater Lake National Park
Come at least once to see the pristine blue water, snowy bluffs and alpine splendor of this park. Return again to immerse yourself in its beauty.
Oregon Shakespeare Festival
You can make plans for a show at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.
Crater Lake
Commune with nature and explore the great outdoors at Crater Lake during your travels in Crater Lake. Stroll along the lakeside or discover the area's volcano viewpoints.
What to do in Southern Oregon
Southern Oregon Hotel Deals
Rogue Regency Inn Medford Airport
2300 Biddle Rd Medford OR
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $95 total per night from May 11 to May 12
$95 total
May 11 - May 12
Total with taxes and fees
8.8/10 Excellent! (2,999 reviews)
Wifi didn't work, room wasn't in good condition, bed was old and uncomfortable, pillows were terrible and one had a hard RFID tag in it. You could hear everyone in the hallway and every door that shut. Breakfast was super subpar, which is the whole reason I booked it. I paid $120 and would value ...
Reviewed on May 10, 2026
Compass by Margaritaville in Medford
2399 S Pacific Hwy Medford OR
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $183 total per night from May 11 to May 12
$183 total
May 11 - May 12
Total with taxes and fees
9.6/10 Exceptional! (1,016 reviews)
I really enjoyed our stay here, but through Expedia, I rented an ADA room, but when I arrived they had no knowledge of the request. They were able to find us a room with a walk in shower, but it had no safety bars, so I was not able to use it. Next time, I will not go through Expedia, but will reserve ...
Reviewed on May 9, 2026
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $143 total per night from May 31 to Jun 1
$143 total
May 31 - Jun 1
Total with taxes and fees
8.8/10 Excellent! (1,471 reviews)
Nice
Reviewed on May 8, 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.
Find the Best Southern Oregon Vacation Packages
Southern Oregon Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rogue Valley Intl. Airport (MFR) |
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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.
