Southern Oregon Vacation Packages 2026 from $635

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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.

McCall House Boutique Inn

Historic Downtown District

$635

per person

Oct 26 - Oct 28

found 1 day ago

Roundtrip non-stop flight included

Fresno (FAT) to Medford (MFR)

9.2/10 Wonderful! (608 reviews)

Savage Upon Siskiyou

Siskiyou-Hargadine Historic District

$1,598

per person

Dec 14 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Medford (MFR)

10/10 Exceptional! (2 reviews)

Had an amazing stay, thank you!

Reviewed on Aug 5, 2026

Hummingbird Estate Wine & Suites

$994

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.6/10 Exceptional! (185 reviews)

A converted estate that oozes with characters and charms in a beautiful surroundings, we were very happy to have found this place. The whole suit is spacious, bedroom and a separate living room. All the rooms have lots of windows that look out to the beautiful vineyard. The owners were relaxed and friendly. Highly recommend to stay for more than one day to relax and enjoy the wine and soak in the surroundings.

Reviewed on Sep 23, 2026

Hanna's House by WanderLodges

Historic Railroad District

$918

per person

Dec 14 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Medford (MFR)

10/10 Exceptional! (4 reviews)

Next visit to the OSF no question we’ll stay here if available. Short walking distance to everything in downtown Ashland, yet quiet and private.

Reviewed on Aug 2, 2026

Winchester Inn

Historic Downtown District

$937

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.6/10 Exceptional! (285 reviews)

The property is very charming, and comfortable with beautiful gardens and outdoor spaces. The breakfast choices were delicious and dinner was also exceptional. Staff is very warm, friendly and helpful. I recommend highly.

Reviewed on Sep 21, 2026

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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 Baldwin Hotel Museum or Upper Klamath Lake 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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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

$164 nightly

$183 total

Oct 12 - Oct 13

Total with taxes and fees

9.6/10 Exceptional! (1,140 reviews)

"Great stay!! Our only issue is there isn't enough parking. We stayed on a Mon, Tue night and had to park in the far back and it looked like we got the only spot left. Th hotel is next to a casino and it seems the people are parking at the hotel as overflow. This is the only reason we might not be ..."

Reviewed on Sep 23, 2026

Riverside Inn

986 S.W. 6th Grants Pass OR

Fully refundableReserve now, pay when you stay

$129 nightly

$146 total

Oct 19 - Oct 20

Total with taxes and fees

Red Lion Hotel Rogue Regency Medford Airport

2300 Biddle Rd Medford OR

Fully refundableReserve now, pay when you stay

$93 nightly

$104 total

Sep 26 - Sep 27

Total with taxes and fees

8.6/10 Excellent! (3,257 reviews)

"The room stunk and we got put on the first floor which is pretty much the basement, WiFi didn’t work down there so the TV didn’t work. Shower had hair everywhere and the beds are blown out. I will not stay here again."

Reviewed on Sep 23, 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.