O'Brien Vacations from $652

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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.
Prospero's Flagship Inn

Prospero's Flagship Inn

2.5 out of 5
Price was $778, price is now $652 per person
$652
per person
Jan 26 - Feb 2
found 16 hours ago
Roundtrip flight included
Phoenix (PHX) to Medford (MFR)
8.4/10 Very Good! (1,487 reviews)
As always, customer service went above and beyond from the kiosk to the breakfast attendant, the night receptionist and the maids everybody was on point. The Mexican restaurant next-door is great. I had a week stay for work and everything was not too much not too little but just right. The price is so good. I couldn’t find a better one from Medford to Yreka. Even Motel 6 wanted hundreds of dollars more! Don’t stay at other places stay here, great parking, hot water, clean rooms, comfortable beds great location I could go on and on.

Reviewed on Nov 12, 2026

Winchester Inn

Winchester Inn

3.5 out of 5
Historic Downtown District
Price was $1,214, price is now $1,021 per person
$1,021
per person
Jan 26 - Feb 2
found 16 hours ago
Roundtrip flight included
Phoenix (PHX) to Medford (MFR)
9.6/10 Exceptional! (291 reviews)
Well maintained and beautiful Victorian boutique hotel located within a short walk to Main Street. Our room had all the modern amenities. Staff very helpful. Breakfast was good.

Reviewed on Nov 10, 2026

Savage Upon Siskiyou

Savage Upon Siskiyou

3 out of 5
Siskiyou-Hargadine Historic District
Price was $1,460, price is now $1,237 per person
$1,237
per person
Jan 26 - Feb 2
found 16 hours ago
Roundtrip flight included
Phoenix (PHX) to Medford (MFR)
10/10 Exceptional! (2 reviews)
Had an amazing stay, thank you!

Reviewed on Aug 5, 2026

Grandview of Ashland

Grandview of Ashland

3 out of 5
Price was $1,528, price is now $1,303 per person
$1,303
per person
Jan 26 - Feb 2
just found
Roundtrip flight included
Phoenix (PHX) to Medford (MFR)
10/10 Exceptional! (11 reviews)
This property was absolutely magic! The home is incredibly beautiful and welcoming. The property owners were incredibly easy to communicate with and we felt like we were at a resort. The surroundings are stunning and while you feel completely removed from everything you are just minutes from OSF in Ashland. From drinking coffee while watching deer in the yard to just taking in the panoramic gorgeous views, we didn't want to leave the house. I honestly can not wait to use it again!

Reviewed on Oct 11, 2026

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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
$271 nightly
The price is $275 total per night from Nov 14 to Nov 15
$275 total
Nov 14 - Nov 15
Total with taxes and fees
9.8/10 Exceptional! (30 reviews)
"We come here reguraly. Tis place is great, clean, and friendly. We usually grab the lodge and our Kids grab individual cabins. The Lodge is a great home base. we have a great time and always have big family dinners. Christopher is super friendly and very accomadating. He went to great lengths to ..."

Reviewed on Oct 9, 2026

The Lodge - 3 bedroom, 2 bath Large Resort Cabin - Sleep Six easily. Call if you have more than six.
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
$109 nightly
The price is $111 total per night from Nov 14 to Nov 15
$111 total
Nov 14 - Nov 15
Total with taxes and fees
9.2/10 Wonderful! (7 reviews)
"The first cabin we stayed in smelled like cigarette smoke. However, the host was very accommodating and quickly helped us move to a different cabin. We really enjoyed our stay, loved the beautiful property, and appreciated the excellent customer service. We would definitely stay here again."

Reviewed on Jul 10, 2026

Applegate Cabin 2 - Restrooms and Showers are only a short walk away.
Buck and Does - 20' - Sleeps up to 4 - Restrooms and Showers are only a short walk away.

Buck and Does - 20' - Sleeps up to 4 - Restrooms and Showers are only a short walk away.

O'Brien OR
$114 nightly
The price is $116 total per night from Nov 14 to Nov 15
$116 total
Nov 14 - Nov 15
Total with taxes and fees
10/10 Exceptional! (6 reviews)
"Such a cute place and fun experience. The pond was perfect!"

Reviewed on Sep 25, 2026

Buck and Does - 20' - Sleeps up to 4 - 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

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Frequently asked questions

How much does an O'Brien vacation package cost?
You'll find cheap prices from $652 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.