O'Brien Vacations from $628

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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.
My Place Hotel-Medford OR

My Place Hotel-Medford OR

3 out of 5
Price was $728, price is now $628 per person
$628
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Medford (MFR)
9.2/10 Wonderful! (1,580 reviews)
I always stay here whenever I’m in town and love their rooms and parking lot. The staff is always so kind and quick when checking in and out. Cute little place to stay at by the airport too.

Reviewed on Jul 15, 2026

Winchester Inn

Winchester Inn

3.5 out of 5
Historic Downtown District
Price was $1,812, price is now $1,364 per person
$1,364
per person
Sep 3 - Sep 7
found 21 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Medford (MFR)
9.6/10 Exceptional! (276 reviews)
Good location. Good breakfast

Reviewed on Jul 14, 2026

A Cowslip's Belle Inn

A Cowslip's Belle Inn

3 out of 5
Price was $987, price is now $815 per person
$815
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Medford (MFR)
9.6/10 Exceptional! (46 reviews)
We stayed in the upper appartment. The place is beautiful, comfortable, quite, and clean. The kitchen is well equipped. The balcony overlooks a beautiful garden patio. The location is a short walking distance to Ashlands' center with its theaters, coffee shops and restaurants. Steve, our host, was welcoming, bery communicative and accessible. Our stay was perfect.

Reviewed on Jun 25, 2026

The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2 out of 5
Historic Railroad District
Price was $1,091, price is now $914 per person
$914
per person
Sep 3 - Sep 7
found 21 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Medford (MFR)
9.6/10 Exceptional! (109 reviews)
We loved our stay at The Peerless. The room was beautiful and comfortable and the hotel’s lobby, back room, and patio are lovely for hanging out in. The in-room coffee needs filters and a suggestion of amount for those of us who are coffee making impaired. We would stay here again!

Reviewed on Jun 27, 2026

Hanna's House by WanderLodges

Hanna's House by WanderLodges

4 out of 5
Historic Railroad District
Price was $1,358, price is now $1,147 per person
$1,147
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Oklahoma City (OKC) to Medford (MFR)
10/10 Exceptional! (3 reviews)
Thoughtfully arranged and provisioned. A hidden gem.

Reviewed on Dec 14, 2025

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O'Brien Hotel Deals

Sky Spirit -Luxury Glamping 18' Tipi - Restrooms and Showers are only a short walk away.

Sky Spirit -Luxury Glamping 18' Tipi - Restrooms and Showers are only a short walk away.

O'Brien OR
$139 nightly
The price is $141 total per night from Jul 18 to Jul 19
$141 total
Jul 18 - Jul 19
Total with taxes and fees
10/10 Exceptional! (6 reviews)
"The place was very clean and it was easy to operate all the amenities the host was very nice and very helpful would stay there again"

Reviewed on Jul 13, 2026

Sky Spirit -Luxury Glamping 18' Tipi - Restrooms and Showers are only a short walk away.
Gold Creek Cabin 3 - Restrooms and Showers are only a short walk away.

Gold Creek Cabin 3 - Restrooms and Showers are only a short walk away.

O'Brien OR
$142 nightly
The price is $144 total per night from Jul 18 to Jul 19
$144 total
Jul 18 - Jul 19
Total with taxes and fees
9.6/10 Exceptional! (7 reviews)
"Great place to come and relax, the swimming pond is amazing."

Reviewed on Jul 4, 2026

Gold Creek Cabin 3 - Restrooms and Showers are only a short walk away.
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
$289 nightly
The price is $293 total per night from Jul 18 to Jul 19
$293 total
Jul 18 - Jul 19
Total with taxes and fees
9.8/10 Exceptional! (27 reviews)
"My wife and I and our two dogs booked The Lodge for 6 nights. The cabin was very nice and roomy. It could easily sleep 6 as advertised. The campground was the quietest we have every been to. There's a pond on the property that our dogs loved to play in. We had an awesome experience overall. The perfect ..."

Reviewed on Jul 4, 2026

The Lodge - 3 bedroom, 2 bath Large Resort Cabin - Sleep Six easily. Call if you have more than six.
See all 46 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 $628 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.