O'Brien Vacations from $389

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.
Wine Country Inn

Wine Country Inn

3 out of 5
Price was $459, price is now $389 per person
$389
per person
Jun 5 - Jun 7
found 21 hours ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.4/10 Exceptional! (1,001 reviews)
Great location. Walking distance to downtown. Nice selection of morning snacks

Reviewed on Mar 16, 2026

A Cowslip's Belle Inn

A Cowslip's Belle Inn

3 out of 5
Price was $591, price is now $491 per person
$491
per person
Jun 5 - Jun 7
found 21 hours ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.8/10 Exceptional! (41 reviews)
Lovely yard courtyard area with koi pond

Reviewed on Aug 25, 2025

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was $548, price is now $468 per person
$468
per person
Apr 15 - Apr 17
found 3 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.2/10 Wonderful! (590 reviews)
Nice job on the room, service.

Reviewed on Mar 16, 2026

Selah House in Jacksonville

Selah House in Jacksonville

2 out of 5
Price was $985, price is now $854 per person
$854
per person
Jun 5 - Jun 7
found 21 hours ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to O'Brien
View all trips

Discover the most popular places to visit in O'Brien

CAVE JUNCTION, OREGON, UNITED STATES - Sep 30, 2019: Cave entrance at Oregon Caves National Monument

Oregon Caves National Monument

4.5/5(37 reviews)

Commune with nature and explore the great outdoors at Oregon Caves National Monument during your travels in Cave Junction. Wander the forest or discover the area's waterfalls.

Oregon Caves National Monument
Leopard, beautiful portrait . Animal world. Big cat.

Great Cats World Park

Meet the animals who live at Great Cats World Park during your travels in Cave Junction. Wander the parks or discover the area's mountain views.

Great Cats World Park

Rough and Ready Flat Botanical Area

Explore the great outdoors at Rough and Ready Flat Botanical Area, a lovely green space in Cave Junction. Stroll along the lakeside or discover the area's waterfalls.

Rough and Ready Flat Botanical Area

O'Brien Hotel Deals

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

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

O'Brien OR
$289 nightly
The price is $293 total per night from Mar 17 to Mar 18
$293 total
Mar 17 - Mar 18
Total with taxes and fees
9.8/10 Exceptional! (25 reviews)
The Lodge was nothing short of perfect for our family getaway for Thanksgiving! Fully stocked, gorgeous property, comfortable beds, the bathtub 😍, and Mr. Love was able to answer any questions we had. You can see the pride he has in the property and The Lodge. Can't wait to visit again!

Reviewed on Nov 30, 2025

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

Augustino Vineyard Winery Cabin Cave Junction

O'Brien OR
$197 nightly
The price is $199 total per night from Mar 17 to Mar 18
$199 total
Mar 17 - Mar 18
Total with taxes and fees
10/10 Exceptional! (1 review)
Beautiful stay

Reviewed on Nov 7, 2025

Augustino Vineyard Winery Cabin Cave Junction
Summer Trail Cabin 5 - Restrooms and Showers are only a short walk away.

Summer Trail Cabin 5 - Restrooms and Showers are only a short walk away.

O'Brien OR
$142 nightly
The price is $144 total per night from Mar 17 to Mar 18
$144 total
Mar 17 - Mar 18
Total with taxes and fees
Summer Trail Cabin 5 - Restrooms and Showers are only a short walk away.
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.

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an O'Brien vacation package cost?
You'll find cheap prices from $389 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.