Milwaukie Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Gabriel Rahl

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Milwaukie

Find the best Milwaukie areas and neighborhoods for the activities you enjoy most. Learn more about Milwaukie
Default Image

Oak Grove

1 out of top 10 points of interest in this area

You'll enjoy the cafes and shopping in Oak Grove. You might want to make time for a stop at Willamette River or Bike N Hike.

Find hotels in Oak Grove

Find the Best Milwaukie Vacation Packages

Milwaukie Hotel Deals

Courtyard by Marriott Portland City Center

Courtyard by Marriott Portland City Center

3.5 out of 5
550 SW Oak Street, Portland, OR
Fully refundable
The price is ₩153,100 per night from Jul 27 to Jul 28
₩153,100
₩179,371 total
Jul 27 - Jul 28
includes taxes & fees
8.6/10 Excellent! (1,865 reviews)
"Central location but sketchy area"

Reviewed on Jul 23, 2025

Courtyard by Marriott Portland City Center
Red Lion Hotel Portland Airport

Red Lion Hotel Portland Airport

3 out of 5
7101 NE 82nd Ave, Portland, OR
Fully refundableReserve now, pay when you stay
The price is ₩126,391 per night from Aug 10 to Aug 11
₩126,391
₩147,333 total
Aug 10 - Aug 11
includes taxes & fees
7.6/10 Good! (2,470 reviews)
"This is an older hotel that was remodeled at some point. It is showing its age again, but, it was convenient to the Airport, a lower price point, and it was clean. If you are planning to fly out of the Portland airport, or flying in, and just need a bed to sleep in for the night - this is a great ..."

Reviewed on Jul 22, 2025

Red Lion Hotel Portland Airport
The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St, Portland, OR
Fully refundableReserve now, pay when you stay
The price is ₩154,890 per night from Jul 27 to Jul 28
₩154,890
₩180,540 total
Jul 27 - Jul 28
includes taxes & fees
9.2/10 Wonderful! (2,631 reviews)
"Walkable but a little sketchy at night."

Reviewed on Jul 23, 2025

The Paramount Hotel
See all 2,795 properties in Milwaukie
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.

Discover the most popular places to visit in Milwaukie

Powell\'s City of Books which includes interior views

Powell's City of Books

Perfect for a rainy-day visit, this famous bookstore is a wonderful spot to visit any day. Browse for hours amid its 1 million books.

Powell's City of Books
Tom McCall Waterfront Park featuring a bridge, bird life and a river or creek

Tom McCall Waterfront Park

Cool off in the fountain, walk or bike the paths, or take in a festival at the Tom McCall Waterfront Park.

Tom McCall Waterfront Park
Pioneer Courthouse Square featuring heritage architecture, a city and outdoor eating

Pioneer Courthouse Square

Portland’s downtown “living room” is a beloved town square and a symbol of the city’s commitment to lively public spaces.

Pioneer Courthouse Square

Frequently asked questions

How much does a Milwaukie vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Milwaukie costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Milwaukie?
January, February and April are the best times to search for cheap Milwaukie vacation packages. Opting to travel in less busy periods means you can generally find better prices on hotels and flights.
How many days is enough for Milwaukie?
Milwaukie vacations come in all shapes and sizes, but to really get a feel for this destination, we'd say 2 days is a good ballpark. This will mean you can visit top attractions like North Clackamas Aquatic Park and Milwaukie Farmers Market and seek out some hidden gems. Don't forget to explore cool neighborhoods such as Downtown Portland and Lloyd District either. If you're smart with your time, you can even take a day trip outside of Milwaukie too.
Is it worth booking a vacation package to Milwaukie?
Whether you'd like to explore top attractions like Waverley Country Club and North Clackamas Aquatic Park on your Milwaukie vacation, or coming for its excellent shopping, distilleries and craft breweries and bars and pubs, there's something for everyone here. With so much to see and do, you'll soon learn why so many visitors think Milwaukie is a good vacation destination.
How to find the best Milwaukie package deals?
Use Expedia's filters to help you find some great Milwaukie package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Milwaukie package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Milwaukie vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Milwaukie vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Milwaukie?
If you have your Milwaukie travel dates confirmed, book as early as you can to grab some outstanding deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for traveling on a whim.
How to plan a trip to Milwaukie?

  1. Choose your travel dates: The things you want to do in Milwaukie and your favorite season will help you decide when to get away.
  2. Budget wisely: Besides the price of your accommodations, you'll need to factor in other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that may come up during your trip to Milwaukie.
  3. Decide how long to go away for: Now that you're more familiar with Milwaukie, you can work out the perfect length of your break. Create a draft plan and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodations: After you've settled on your trip dates and duration, lock in the ideal Milwaukie vacation package for you.

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