O'Brien Vacations from $292

Book a Hotel + Flight or Car together to unlock savings

Photo by Corvid Drifter

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 $405, price is now $292 per person
$292
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
8/10 Very Good! (1,077 reviews)
Didn’t make my reservation. Plane flight got cancelled

Reviewed on Dec 9, 2025

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $523, price is now $398 per person
$398
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.6/10 Exceptional! (1,003 reviews)
Friendly staff. Upbeat atmosphere. Clean. Nice happy hour.

Reviewed on Nov 27, 2025

A Cowslip's Belle Inn

A Cowslip's Belle Inn

3 out of 5
Price was $506, price is now $391 per person
$391
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.8/10 Exceptional! (40 reviews)
Lovely yard courtyard area with koi pond

Reviewed on Aug 25, 2025

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
Price was $556, price is now $441 per person
$441
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.2/10 Wonderful! (1,000 reviews)
We enjoyed our visit immensely. The room isn’t designed for someone who wants to work from their room, but it was perfect for a vacation. The room was beautiful, the service was great, the restaurant was delicious. We were blocks from the Shakespeare festival and steps from several great restaurants and amazing shops.

Reviewed on Dec 7, 2025

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was $569, price is now $454 per person
$454
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.2/10 Wonderful! (574 reviews)
The room and the breakfast. The staff were very nice.

Reviewed on Nov 23, 2025

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Discover the most popular places to visit in O'Brien

Great hiking trails #caves #oregon #pretty #forest

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

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

Siskiyou Smokejumper Base Museum

You can spend an afternoon exploring the galleries in Siskiyou Smokejumper Base Museum during your trip to Cave Junction. Take in the museums and mountain views in the area.

Siskiyou Smokejumper Base Museum

O'Brien Hotel Deals

Augustino Vineyard Winery Cabin Cave Junction

Augustino Vineyard Winery Cabin Cave Junction

O'Brien OR
$199 nightly
The price is $201 total per night from Dec 16 to Dec 17
$201 total
Dec 16 - Dec 17
Total with taxes and fees
Beautiful stay

Reviewed on Nov 7, 2025

Augustino Vineyard Winery Cabin Cave Junction
Reconnect with nature at this unforgettable escape

Reconnect with nature at this unforgettable escape

O'Brien OR
$145 nightly
The price is $147 total per night from Dec 11 to Dec 12
$147 total
Dec 11 - Dec 12
Total with taxes and fees
10/10 Exceptional! (1 review)
This was a really great place to stay and visit relatives in Cave Junction. We loved the layout of the RV, and the park was very clean and had nice amenities. The RV was clean and the AC was on when we arrived which was great. It was very well appointed and pet friendly. Loved the deck! I didn’t ...

Reviewed on Jul 10, 2025

Reconnect with nature at this unforgettable escape
Applegate Cabin 2 - Restrooms and Showers are only a short walk away.

Applegate Cabin 2 - Restrooms and Showers are only a short walk away.

O'Brien OR
$114 nightly
The price is $116 total per night from Dec 11 to Dec 12
$116 total
Dec 11 - Dec 12
Total with taxes and fees
9/10 Wonderful! (4 reviews)
Exceeded expectations
The whole RV resort was well-maintained and quiet. The bathrooms were cleaner than I could have ever expected. Communication was very easy and straight forward. I look forward to staying here again!

Reviewed on Jun 27, 2025

Applegate Cabin 2 - Restrooms and Showers are only a short walk away.
See all 43 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 $292 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.