O'Brien Vacations from $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
$443
per person
Nov 27 - Dec 2
found 21 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 Oct 16, 2026
Kubli Haus
$888
per person
Nov 27 - Dec 2
found 21 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 Oct 16, 2026
Hanna's House by WanderLodges
Historic Railroad District
$577
per person
Nov 27 - Dec 2
found 21 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 Oct 4, 2026
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
$316 nightly
$321 total
Oct 21 - Oct 22
Total with taxes and fees
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 Oct 9, 2026
Applegate Cabin 2 - Restrooms and Showers are only a short walk away.
O'Brien OR
$123 nightly
$125 total
Oct 21 - Oct 22
Total with taxes and fees
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 Jul 10, 2026
Buck and Does - 20' - Sleeps up to 4 - Restrooms and Showers are only a short walk away.
O'Brien OR
$133 nightly
$135 total
Oct 21 - Oct 22
Total with taxes and fees
10/10 Exceptional! (6 reviews)
"Such a cute place and fun experience. The pond was perfect!"
Reviewed on Sep 25, 2026
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.
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 |
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Frequently asked questions
How much does an O'Brien vacation package cost?
You'll find cheap prices from $443 on Expedia for your O'Brien getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to O'Brien costs.
What are the cheapest months to go to O'Brien?
February, October and December are the best times to look for cheap O'Brien vacation packages. Traveling in less busy months means you'll typically find reduced prices on accommodations and flights.
How many days is enough for O'Brien?
Usually, a handful of days is enough to explore the main attractions during your O'Brien vacation. But if you prefer to have time to rest or take day tours, think about extending your itinerary.
How to find the best O'Brien package deals?
Use Expedia's filters to help you find some of the best O'Brien package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for O'Brien package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book an O'Brien vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and hotels separately. Better still, you can customize your O'Brien trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to O'Brien?
If you have your O'Brien vacation dates confirmed, book as early as you can to snap up some fantastic deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for traveling on a whim.
Does Expedia offer Book Now, Pay Later O'Brien vacation packages?
Your O'Brien break is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to give you more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
