Southern Oregon Vacations from $305
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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.
A Cowslip's Belle Inn
Save 100% on your flight
per person
Sep 19 - Sep 22
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.8/10 Exceptional! (34 reviews)
What a wonderful place to stay! The owners were very cordial and offered suggestion about places to go. We particularly loved to Koi pond right off our deck.
Reviewed on Jul 28, 2025
Wine Country Inn
per person
Sep 19 - Sep 22
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.4/10 Exceptional! (1,001 reviews)
Great location. We walked to the center of town in just a few minutes. Very clean. And what a great town!! It was also a great surprise to have an EV charger in the parking lot. It’s not a high speed charger but on our last night in town, I plugged in and charged my car overnight like I do at home. And we were ready for the next part of our trip. Saved us a half an hour of travel time!
Reviewed on Aug 5, 2025
Paschal Winery
per person
Sep 19 - Sep 22
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.6/10 Exceptional! (10 reviews)
It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland.
Reviewed on May 3, 2025
Compass by Margaritaville in Medford
per person
Sep 19 - Sep 22
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.6/10 Exceptional! (931 reviews)
Best hotel in Oregon! Wish you had more locations! Loved the clean room and friendly staff! The breakfast buffet was great. Our go to hotel in Medford!
Reviewed on Aug 6, 2025
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(133 area reviews)
If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival 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 and Suites
2300 Biddle Rd, Medford, OR
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $135 total per night from Aug 12 to Aug 13
$135 total
Aug 12 - Aug 13
Total includes taxes and fees
8.8/10 Excellent! (2,224 reviews)
"The hotel is decent, clean, close to lots of shopping and dinning options, easy parking. The bed was comfortable, that staff was ok, the continental breakfast was ok and their indoor pool is ok."
Reviewed on Aug 6, 2025
Flagship Inn of Ashland
1193 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $82 total per night from Aug 20 to Aug 21
$82 total
Aug 20 - Aug 21
Total includes taxes and fees
8.8/10 Excellent! (1,019 reviews)
"Great place to stay with family on a roadtrip!"
Reviewed on Aug 6, 2025
Cerulean Hotel
100 Main St, Klamath Falls, OR
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $124 total per night from Aug 19 to Aug 20
$124 total
Aug 19 - Aug 20
Total includes taxes and fees
8.8/10 Excellent! (338 reviews)
"Outside appearance is not appealing. However, the room was spacious and comfortable. The room was very nice."
Reviewed on Aug 3, 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.