Southern Oregon Vacation Packages 2026 from $1,041

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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.

Winchester Inn

Historic Downtown District

$1,041

per person

Nov 9 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Medford (MFR)

9.6/10 Exceptional! (283 reviews)

Everything was perfect

Reviewed on Aug 6, 2026

McCall House Boutique Inn

Historic Downtown District

Save 100% on your flight

$1,527

per person

Oct 10 - Oct 17

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.2/10 Wonderful! (605 reviews)

Cute place. Helpful and friendly staff. Excellent breakfast. Would definitely return because I’m already booked again.

Reviewed on Aug 28, 2026

Meadowsweet Farm by WanderLodges

Save 100% on your flight

$2,254

per person

Nov 9 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Medford (MFR)

No reviews

Rosewood Collective- House & Studio

$1,634

per person

Oct 15 - Oct 21

found 7 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Medford (MFR)

No reviews

Rosewood Landing- Hot Tub- Sauna

$1,506

per person

Oct 15 - Oct 21

found 7 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Medford (MFR)

No 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 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 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.

An aerial view of a town with a river, surrounded by mountains and autumn-colored trees.

City Center Medford

Travelers come to City Center Medford for its abundant dining options, and you can see top attractions like Medford Central Library and Medford City Hall while you're in town.

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.

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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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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Rogue Valley Mall

8.2/10 (554 reviews)

Southern Oregon's largest indoor shopping center offers over 100 specialty stores and major retailers. Browse diverse shops and recharge at the food court during your Medford retail adventure.

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Britt Pavilion

9.6/10 (43 reviews)

This hillside amphitheater hosts the renowned Britt Music & Arts Festival amid towering ponderosa pines. Bring a blanket for lawn seating and enjoy world-class performances under starlit Oregon skies.

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Running Y Ranch Golf Course

8.4/10 (140 reviews)

Oregon's only Arnold Palmer-designed course blends natural beauty with strategic challenges. Enjoy well-maintained fairways while taking in scenic views of meadows, woodlands, and wetlands throughout your round.

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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

$171 nightly

$191 total

Sep 21 - Sep 22

Total with taxes and fees

9.6/10 Exceptional! (1,077 reviews)

"Clean room, staff and breakfast"

Reviewed on Aug 28, 2026

Rogue Regency Inn Medford Airport

2300 Biddle Rd Medford OR

Fully refundableReserve now, pay when you stay

$122 nightly

$137 total

Sep 26 - Sep 27

Total with taxes and fees

Comfort Inn & Suites Ashland

434 S. Valley View Rd. Ashland OR

Fully refundable

$105 nightly

$107 total

Sep 28 - Sep 29

Total with taxes and fees

9/10 Wonderful! (1,004 reviews)

"Very comfortable room and view of the hills. Easy access to the Shakespeare Festival."

Reviewed on Aug 28, 2026

See all 1,444 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.