O'Brien Vacations from $705
Book a Hotel + Flight or Car together to unlock savings
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.
Hummingbird Estate Wine & Suites
$828
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Medford (MFR)
9.6/10 Exceptional! (185 reviews)
Very cute winery and we had tickets for free drinks because we were staying in the rooms. Clean but the air conditioning did leak onto the floor both nights and the outlet in the bathroom did not work making it difficult to get ready. Would stay again.. just needs a little updating.
Reviewed on Sep 16, 2026
Winchester Inn
Historic Downtown District
$958
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Medford (MFR)
9.6/10 Exceptional! (285 reviews)
Our stay at the Winchester Inn was very pleasant and enjoyable. The complimentary made to order breakfast was delicious, and the room was very comfortable and quiet. The location was very convenient and walkable to downtown's many excellent restaurants and the Shakespeare Festival. Would definitely stay there again.
Reviewed on Sep 5, 2026
The Bard's Inn, BW Signature Collection by Best Western
Historic Downtown District
$805
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Medford (MFR)
8.6/10 Excellent! (1,001 reviews)
The room was clean, but had only one bar of soap at the sink, and none in the bathroom. There were very few towels, and one was very worn with stings hanging at the ends. When I asked for a new towel, the staff was real nice. The woman who checked me in was lovely. Breakfast was okay. Parking was tight but goid enough. I would stay there again but bring my own soap.
Reviewed on Sep 16, 2026
O'Brien Hotel Deals
Augustino Vineyard Winery Cabin Cave Junction
O'Brien OR
$282 nightly
$285 total
Sep 20 - Sep 21
Total with taxes and fees
10/10 Exceptional! (5 reviews)
"The cabin was in pristine condition complete with outdoor motif. Wine tasting treehouse is right at the property as well. FABULOUS"
Reviewed on Sep 12, 2026
Sky Spirit -Luxury Glamping 18' Tipi - Restrooms and Showers are only a short walk away.
O'Brien OR
$138 nightly
$140 total
Sep 20 - Sep 21
Total with taxes and fees
10/10 Exceptional! (7 reviews)
"Very cool experience staying in the tipi! Clean and comfortable. Peaceful, beautiful location close to the Oregon Caves. Management is friendly and quick to communicate."
Reviewed on Sep 9, 2026
The Lodge - 3 bedroom, 2 bath Large Resort Cabin - Sleep Six easily. Call if you have more than six.
O'Brien OR
$294 nightly
$299 total
Sep 20 - Sep 21
Total with taxes and fees
9.8/10 Exceptional! (29 reviews)
"Great place"
Reviewed on Aug 18, 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 $705 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.