O'Brien Vacations from $259

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.
Super 8 by Wyndham Central Pt Medford

Super 8 by Wyndham Central Pt Medford

2 out of 5
Price was $360, price is now $259 per person
$259
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
7.2/10 Good! (1,012 reviews)
The staff was very helpful and courteous

Reviewed on Sep 26, 2025

Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $595, price is now $423 per person
$423
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
9.6/10 Exceptional! (136 reviews)
Vineyard and the hummingbirds buzzing around were amazing!

Reviewed on Sep 22, 2025

Wine Country Inn

Wine Country Inn

3 out of 5
Price was $448, price is now $327 per person
$327
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
9.4/10 Exceptional! (1,004 reviews)
We enjoyed the room and Jacksonville very much

Reviewed on Sep 26, 2025

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Save 100% on your flight
Price was $807, price is now $621 per person
$621
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
9.2/10 Wonderful! (571 reviews)
Very welcoming and hospitable staff. The breakfasts are delish, especially the fritata. Their attention to details are very strong.

Reviewed on Aug 15, 2025

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges

4 out of 5
Price was $651, price is now $504 per person
$504
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
10/10 Exceptional! (6 reviews)
One can truly enjoy family time & dinners ~ kitchen is beautifully equipped ⚜️❄️~ Dining room ~ gorgeous ~ open concept makes space perfect 👍

Reviewed on Nov 18, 2024

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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

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

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

Bridgeview Vineyard and Winery

You can enjoy a tasting or tour at Bridgeview Vineyard and Winery during your travels to Cave Junction. Wander the forest or discover the area's waterfalls.

Bridgeview Vineyard and Winery

O'Brien Hotel Deals

Out 'N' About Treehouse Treesort

Out 'N' About Treehouse Treesort

2.5 out of 5
300 Page Creek Rd, Cave Junction, OR
$211 nightly
The price is $215 total per night from Sep 29 to Sep 30
$215 total
Sep 29 - Sep 30
Total with taxes and fees
9.8/10 Exceptional! (7 reviews)
What an Overnight Adventure!
"This was the greatest overnight of any of our family trips, ever, anywhere, no comparison. The treehouses are amazing, the staff are treerific and the breakfast was treemendous. Seriously, this place just takes the whole trip up a notch! I highly recommend the zip lines adventure. We will never forget ..."

Reviewed on Sep 20, 2025

Out 'N' About Treehouse Treesort
Reconnect with nature at this unforgettable escape

Reconnect with nature at this unforgettable escape

O'Brien
$153 nightly
The price is $155 total per night from Sep 29 to Sep 30
$155 total
Sep 29 - Sep 30
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
The Lodge - 3 bedroom, 2 bath large resort cabin

The Lodge - 3 bedroom, 2 bath large resort cabin

O'Brien
$270 nightly
The price is $274 total per night from Sep 28 to Sep 29
$274 total
Sep 28 - Sep 29
Total with taxes and fees
9.8/10 Exceptional! (19 reviews)
"The Lodge was even better than expected! Very spacious with large kitchen, dining and living room area for people to hang out together. Large tv and reclining couch to enjoy some late night movies. The host made the whole process very easy and made sure the AC was on when we arrived for comfort."

Reviewed on Aug 19, 2025

The Lodge - 3 bedroom, 2 bath large resort cabin
See all 42 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.

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Frequently asked questions

How much does an O'Brien vacation package cost?
You'll find cheap prices from $259 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.