O'Brien Vacations from $271

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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.
Clarion Pointe Medford

Clarion Pointe Medford

2.5 out of 5
Price was $346, price is now $271 per person
$271
per person
Mar 13 - Mar 16
found 11 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
8/10 Very Good! (1,077 reviews)
The new manager Terra was wonderful.

Reviewed on Jan 19, 2026

Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $491, price is now $345 per person
$345
per person
Mar 13 - Mar 16
found 11 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.6/10 Exceptional! (145 reviews)
A beautiful place to relax and enjoy life. Excellent service at the wine bar. The room was comfortable, clean and overall exceeded expectations.

Reviewed on Jan 4, 2026

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $478, price is now $366 per person
$366
per person
Mar 13 - Mar 16
found 11 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.6/10 Exceptional! (1,003 reviews)
Clean room, friendly staff

Reviewed on Jan 8, 2026

Wine Country Inn

Wine Country Inn

3 out of 5
Price was $397, price is now $310 per person
$310
per person
Mar 13 - Mar 16
found 11 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.4/10 Exceptional! (1,002 reviews)
Staff were friendly, room was cleaning and very nice. The end is also very dog friendly! They give you a blanket for the dog and a dish! Oh, And dog treats and dog bags to pick up the poop! Very, very nice place

Reviewed on Jan 1, 2026

Paschal Winery

Paschal Winery

4.5 out of 5
Price was $419, price is now $332 per person
$332
per person
Mar 13 - Mar 16
found 11 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.6/10 Exceptional! (13 reviews)
It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland.

Reviewed on May 3, 2025

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Discover the most popular places to visit in O'Brien

Oregon Caves National Monument

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

Foris Vineyards

You can enjoy a tasting or tour at Foris Vineyards during your travels to Cave Junction. Wander the forest or discover the area's waterfalls.

Foris Vineyards

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

RV11 XLR - 27' Family Toy Hauler - Sleeps 6

RV11 XLR - 27' Family Toy Hauler - Sleeps 6

O'Brien OR
$133 nightly
The price is $135 total per night from Feb 2 to Feb 3
$135 total
Feb 2 - Feb 3
Total with taxes and fees
RV11 XLR - 27' Family Toy Hauler - Sleeps 6
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
$130 nightly
The price is $132 total per night from Jan 22 to Jan 23
$132 total
Jan 22 - Jan 23
Total with taxes and fees
Summer Trail Cabin 5 - Restrooms and Showers are only a short walk away.
This tipi is a 0 bedroom(s), 1 bathrooms, located in O'Brien, OR.

This tipi is a 0 bedroom(s), 1 bathrooms, located in O'Brien, OR.

O'Brien OR
Get rates
This tipi is a 0 bedroom(s), 1 bathrooms, located in O'Brien, OR.
See all 45 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

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Frequently asked questions

How much does an O'Brien vacation package cost?
You'll find cheap prices from $271 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.