O'Brien Vacation Packages

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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.

Top O'Brien Vacation Deals

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 CA $1,464, price is now CA $1,249 per person
CA $1,249
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Medford (MFR)
8.4/10 Very good! (1,487 reviews)

Winchester Inn

Winchester Inn

3.5 out of 5
Historic Downtown District
Price was CA $2,254, price is now CA $1,926 per person
CA $1,926
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Medford (MFR)
9.6/10 Exceptional! (291 reviews)
Amazing breakfasts, friendly staff, best location

Reviewed on Oct 10, 2026

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was CA $1,953, price is now CA $1,777 per person
CA $1,777
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Medford (MFR)
9.6/10 Exceptional! (1,173 reviews)

Stratford Inn

Stratford Inn

2.5 out of 5
Siskiyou-Hargadine Historic District
Price was CA $1,668, price is now CA $1,523 per person
CA $1,523
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Medford (MFR)
9.4/10 Exceptional! (1,808 reviews)
Sparkling clean as usual, decent choices at breakfast, friendly staff, and great location within easy walking distance of downtown and theaters.

Reviewed on Nov 5, 2026

TownePlace Suites by Marriott Medford

TownePlace Suites by Marriott Medford

3 out of 5
Price was CA $1,689, price is now CA $1,559 per person
CA $1,559
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Medford (MFR)
8.8/10 Excellent! (424 reviews)
Nice kitchen, micro wave, fridge and lots of dining options

Reviewed on Nov 1, 2026

Ready to book your vacation to O'Brien?

 

Choose your dates

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
The price is CA $301 per night from Nov 9 to Nov 10
CA $301
CA $423 total
Nov 9 - Nov 10
includes taxes & 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
The price is CA $114 per night from Nov 6 to Nov 7
CA $114
CA $167 total
Nov 6 - Nov 7
includes taxes & 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
The price is CA $120 per night from Nov 6 to Nov 7
CA $120
CA $173 total
Nov 6 - Nov 7
includes taxes & 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an O'Brien vacation package cost?
You'll find cheap prices from CA $1,249 on Expedia for your O'Brien getaway. However, factors like the length of stay, hotel choice and season will influence how much your vacation to O'Brien costs.
What are the cheapest months to go to O'Brien?
If you're hoping to book a cheap O'Brien vacation package, consider planning a trip in January, February and March. You're likely to find better rates on hotels and airfares during these quieter months — perfect for travellers wishing to save money.
How many days is enough for O'Brien?
The ideal duration for your O'Brien vacation depends on what you'd like to do. Typically, a few days to a week will give you time to visit all the major sights and explore some hidden treasures along the way.
How to find the best O'Brien package deals?
Begin your search for an O'Brien package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal O'Brien package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your O'Brien escape underway.
Is it cheaper to book an O'Brien vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can customize your O'Brien getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to O'Brien?
Score fantastic discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment O'Brien escape.
How to plan a trip to O'Brien?

  1. Choose when to go: Check your schedule and get your bags packed. Your favourite season and the type of activities available will also help you decide when to visit O'Brien.
  2. Budget wisely: As well as the cost of your stay, you should factor in other expenses too. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that could arise during your trip to O'Brien.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to experience in O'Brien. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick an O'Brien vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.