O'Brien Vacations from $335

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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.
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9/10 Wonderful! (1,476 reviews)
It was a very nice stay. Super cute place.

Reviewed on Aug 11, 2025

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Save 100% on your flight
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.2/10 Wonderful! (566 reviews)
Great location , good breakfast but could use a little modernization

Reviewed on Aug 7, 2025

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.6/10 Exceptional! (937 reviews)
Best hotel in Oregon! Wish you had more locations! Loved the clean room and friendly staff! The breakfast buffet was great. Our go to hotel in Medford!

Reviewed on Aug 6, 2025

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.2/10 Wonderful! (1,006 reviews)
The bed was very comfortable and décor was nice. Easy walk to anything downtown. There was a charger box to charge multiple electronics but it only worked intermittently.

Reviewed on Aug 12, 2025

Lithia Springs Resort

Lithia Springs Resort

3 out of 5
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.4/10 Exceptional! (1,003 reviews)
The grounds used to be kept very nicely and now not so much. The faucet handle in the bathroom was completely unsecure, paint and countertops worn, window seal broken with condensation , carpet on stairs also worn. New resort fee added to the cost of the room in addition to a new charge for what used to be complementary breakfast. Overall, the property has just not been maintained as well as it used to be so the overall experience has been diminished.

Reviewed on Aug 12, 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

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
$207 nightly
The price is $211 total per night from Sep 2 to Sep 3
$211 total
Sep 2 - Sep 3
Total includes taxes and fees
9/10 Wonderful! (2 reviews)
"What a fun and unique place! From the treehouse cabins to the bridges, swing, and zip lines. The natural pool was amazing as well. Oh, and the breakfast!!! Homemade fresh quiche, cheesy potato pie, fresh baked breads, pastries, and eggs. The BEST continental breakfast I have ever seen!!"

Reviewed on Jun 9, 2025

Out 'N' About Treehouse Treesort
Enjoy the Hobbit House! Charming 2-bedroom 1-bathroom house in Kerby, Oregon

Enjoy the Hobbit House! Charming 2-bedroom 1-bathroom house in Kerby, Oregon

Kerby
$128 nightly
The price is $130 total per night from Aug 17 to Aug 18
$130 total
Aug 17 - Aug 18
Total includes taxes and fees
10/10 Exceptional! (4 reviews)
"Check and stay we’re super easy. It’s a very comfy space and we loved the paint scheme of every room being in different color. It’s a very quiet location but is very close to town, like a 2 minute drive. Will definitely stay again next we come up to visit."

Reviewed on Aug 4, 2025

Enjoy the Hobbit House! Charming 2-bedroom 1-bathroom house in Kerby, Oregon
The Lodge - 3 bedroom, 2 bath large resort cabin

The Lodge - 3 bedroom, 2 bath large resort cabin

O'Brien
$287 nightly
The price is $292 total per night from Aug 23 to Aug 24
$292 total
Aug 23 - Aug 24
Total includes taxes and fees
9.8/10 Exceptional! (17 reviews)
nice stay
"The cabin is in a clean, quiet RV park. The manager is very responsive with check in and check out, and was even helpful finding a resource when my daughter had a minor medical issue. The cabin is cute and clean, with plenty of room to spread out. The town is very small with limited options, especially ..."

Reviewed on Jul 29, 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 $335 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.