O'Brien Vacations from $742
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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.
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)
The property, location, and staff were amazing!!! However, the room itself was a little underwhelming due to hearing the upstairs guests all night, the bedroom window opening up to the trash bins, and the shower being extremely cold. Additionally someone woke me up at 3 am drumming on the trash bins, it made me feel unsafe.
Reviewed on Aug 31, 2026
O'Brien Hotel Deals
Augustino Vineyard Winery Cabin Cave Junction
O'Brien OR
$286 nightly
$289 total
Sep 9 - Sep 10
Total with taxes and fees
10/10 Exceptional! (4 reviews)
"Great quiet place in the country. Awesome for relaxing and drinking a glass of wine in the evening."
Reviewed on Jul 29, 2026
Wild Horses Luxury Tipi - Restrooms and Showers are only a short walk away.
O'Brien OR
$138 nightly
$140 total
Sep 3 - Sep 4
Total with taxes and fees
10/10 Exceptional! (2 reviews)
"The stay in the Wild Horse Tipi was everything I expected, and more. The bathrooms were far better than anything I expected to have access to, and were very clean. The host was easy to communicate with, and always available. I will return for another stay, and recommend anyone wishing the tipi experience ..."
Reviewed on Aug 29, 2026
Applegate Cabin 2 - Restrooms and Showers are only a short walk away.
O'Brien OR
$123 nightly
$125 total
Sep 7 - Sep 8
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
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 $742 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.
