Southern Oregon Vacation Packages 2026 from $523

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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.

The Peerless Hotel by WanderLodges

Historic Railroad District

$523

per person

Nov 6 - Nov 10

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.6/10 Exceptional! (114 reviews)

Hummingbird Estate Wine & Suites

Save 100% on your flight

$920

per person

Nov 5 - Nov 10

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.6/10 Exceptional! (186 reviews)

Exceptional spot, unfortunately I was only there for a stopover, but I hope to return soon for a real stay and visit this wonderful region and the winery.

Reviewed on Sep 30, 2026

Kubli Haus

$851

per person

Nov 5 - Nov 10

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

No reviews

Compass by Margaritaville in Medford

$599

per person

Nov 6 - Nov 10

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.6/10 Exceptional! (1,134 reviews)

Winchester Inn

Historic Downtown District

$600

per person

Nov 6 - Nov 10

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.6/10 Exceptional! (288 reviews)

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Where to stay in Southern Oregon

Find the best Southern Oregon areas and neighborhoods for the activities you enjoy most. Learn more about Southern Oregon

A historic building with a classical facade, a person standing on the steps, and a wheelchair-accessible sign.

Historic Downtown District

1 out of top 10 points of interest in this area

If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival are top sights worth seeing.

A tree-lined street with a mountain backdrop.

Siskiyou-Hargadine Historic District

While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.

A mountainous landscape with a large lake, snow-capped peaks, and coniferous trees.

Downtown Klamath Falls

Waterfalls, breweries, and lake views are some highlights of Downtown Klamath Falls. Make a stop by Upper Klamath Lake or Klamath County Museum while you're exploring.

A rusted metal bridge in a forested area.

Historic Railroad District

Historic Railroad District might not have many top sights, but Oregon Cabaret Theatre and Allen Elizabethan Theatre are two attractions nearby that you can check out.

A brick building labeled "City Hall" with a white door and windows, a bench outside, and a tree nearby.

Jacksonville Historic District

Historic sites, restaurants, and shopping highlight some of the noteworthy features of Jacksonville Historic District. Make a stop by Jacksonville Cemetery or Kharmic Creations while you're exploring the neighborhood.

Stay near popular Southern Oregon attractions

A rocky outcrop with a tree stump in the foreground and a calm lake with mountains in the background.

Crater Lake National Park

9.8/10 (578 reviews)

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.

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A statue of a person in a brown outfit with a hat and sunglasses, holding a pipe and a book, standing on a pedestal in a park with green bushes and trees.

Oregon Shakespeare Festival

9.2/10 (620 reviews)

At OSF, America's oldest repertory theater presents Shakespearean classics and bold new works across three venues. Reserve seats for evening performances and arrive early for the free outdoor Green Show entertainment.

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A lake surrounded by mountains and dense forests.

Crater Lake

9.8/10 (286 reviews)

This ancient volcanic caldera holds America's deepest lake, famous for its intense sapphire-blue waters. Take a summer boat tour to Wizard Island or drive the scenic 33-mile rim for unforgettable mountain views.

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A moss-covered rock formation with a staircase leading up and a metal grate at the bottom.

Oregon Caves National Monument

9.4/10 (43 reviews)

Descend into the "Marble Halls of Oregon" with a guided tour through this intricate cave system. Bring a jacket for the cool 44°F interior as you marvel at ancient stalactites and flowstone formations.

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A wood duck standing on rocks with moss and greenery in the background.

Lithia Park

9.6/10 (1,250 reviews)

Stroll through Lithia Park's 93 acres of landscaped beauty alongside Ashland Creek. Discover Japanese gardens, duck ponds, and seasonal foliage while enjoying the serenity of this historic green space.

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Lithia & Driveway Fields

8.4/10 (91 reviews)

Catch an event at Lithia & Driveway Fields during your trip to Medford. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.

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Oregon Institute of Technology - Residential Campus

8.8/10 (138 reviews)

Explore the campus of Oregon Institute of Technology - Residential Campus during your stay in Klamath Falls. Stroll along the lakeside or discover the area's beautiful waterfalls.

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The Expo

8.0/10 (122 reviews)

Southern Oregon's premier event venue hosts everything from trade shows to the beloved Jackson County Fair. Explore seven buildings across 180,000 square feet of dynamic community entertainment.

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Southern Oregon Hotel Deals

Compass by Margaritaville in Medford

2399 S Pacific Hwy Medford OR

Fully refundableReserve now, pay when you stay

$164 nightly

$183 total

Oct 12 - Oct 13

Total with taxes and fees

Red Lion Hotel Rogue Regency Medford Airport

2300 Biddle Rd Medford OR

Fully refundableReserve now, pay when you stay

$98 nightly

$110 total

Oct 20 - Oct 21

Total with taxes and fees

Ashland Hills Hotel & Suites

2525 Ashland St Ashland OR

Fully refundableReserve now, pay when you stay

$121 nightly

$135 total

Nov 2 - Nov 3

Total with taxes and fees

8.8/10 Excellent! (1,532 reviews)

"Overall we enjoyed the stay. Staff was friendly and bed was comfortable. Breakfast was not included which would have been nice."

Reviewed on Sep 30, 2026

See all 1,443 properties in Southern Oregon

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.