O'Brien Vacation Packages 2026 from US$ 443

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Your OBrien Vacation

Memorable adventures await when you reserve a OBrien vacation package. Whether you're a foodie, art buff or just a traveler who loves to discover new places, there's something for everyone in this awesome city. If your trip to OBrien includes some sightseeing, drop by well-known attractions like Illinois River, Great Cats World Park and Bridgeview Vineyard and Winery. Browse Expedia's extensive range of travel options and begin planning your perfect vacation to OBrien now.

The Latest O'Brien Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Wine Country Inn

US$ 443

per person

Nov 27 - Dec 2

found 10 hours ago

Roundtrip flight included

Seattle (SEA) to Medford (MFR)

9.4/10 Exceptional! (1,004 reviews)

The property is so charming and pretty. Staff was really helpful with helping us find somewhere to eat dinner, and their morning breakfast was simple, but had some good choices. I would definitely stay here again!

Reviewed on 16 Oct, 2026

Hummingbird Estate Wine & Suites

US$ 734

per person

Nov 27 - Dec 2

found 10 hours ago

Roundtrip flight included

Seattle (SEA) to Medford (MFR)

9.6/10 Exceptional! (188 reviews)

Ashland Hills Hotel & Suites

US$ 515

per person

Nov 27 - Dec 2

found 10 hours ago

Roundtrip flight included

Seattle (SEA) to Medford (MFR)

8.8/10 Excellent! (1,541 reviews)

Super cute retro hotel with modern updates. I would stay here again!

Reviewed on 20 Oct, 2026

Kubli Haus

US$ 888

per person

Nov 27 - Dec 2

found 10 hours ago

Roundtrip flight included

Seattle (SEA) to Medford (MFR)

No reviews

Kathleen was very helpful and her presence was delightful. Very easy to be around her. there was a little glitch with the Expedia was of doing the reservation which she quickly figured out and she made great recommendations for out stay.

Reviewed on 16 Oct, 2026

Hanna's House by WanderLodges

Historic Railroad District

US$ 577

per person

Nov 27 - Dec 2

found 10 hours ago

Roundtrip flight included

Seattle (SEA) to Medford (MFR)

10/10 Exceptional! (4 reviews)

Very cute cottage, 10 min walk to OSF theaters. It has everything you need - full kitchen, front room, and AC for the hot summers! Owner very kind. Will stay there again!

Reviewed on 4 Oct, 2026

Find the Best O'Brien Vacation Packages

OBrien Essential Information

Language	English
Currency	U.S dollars
Population	500
Top Sights	Great Cats World Park, Foris Vineyards and Tiger Preservation Center

O'Brien Hotel Deals

The Lodge - 3 bedroom, 2 bath Large Resort Cabin - Sleep Six easily. Call if you have more than six.

O'Brien OR

9.8/10 Exceptional! (30 reviews)

"We come here reguraly. Tis place is great, clean, and friendly. We usually grab the lodge and our Kids grab individual cabins. The Lodge is a great home base. we have a great time and always have big family dinners. Christopher is super friendly and very accomadating. He went to great lengths to ..."

Reviewed on 9 Oct, 2026

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Applegate Cabin 2 - Restrooms and Showers are only a short walk away.

O'Brien OR

9.2/10 Wonderful! (7 reviews)

"The first cabin we stayed in smelled like cigarette smoke. However, the host was very accommodating and quickly helped us move to a different cabin. We really enjoyed our stay, loved the beautiful property, and appreciated the excellent customer service. We would definitely stay here again."

Reviewed on 10 Jul, 2026

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Buck and Does - 20' - Sleeps up to 4 - Restrooms and Showers are only a short walk away.

O'Brien OR

10/10 Exceptional! (6 reviews)

"Such a cute place and fun experience. The pond was perfect!"

Reviewed on 25 Sep, 2026

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See all 44 properties in O'Brien

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.