Milwaukie Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Gabriel Rahl

Where to stay in Milwaukie

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

Top hotels in Milwaukie

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
1000 NE Multnomah Street, Portland, OR
Fully refundableReserve now, pay when you stay
The price is 3.108.881 ₫ per night from 2 Sept to 3 Sept
3.108.881 ₫
3.624.023 ₫ total
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (1,016 reviews)
"Great location and close enough to downtown Portland. Loved the warm cookies!"

Reviewed on 20 Aug 2025

DoubleTree by Hilton Hotel Portland
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 2.926.006 ₫ per night from 22 Aug to 23 Aug
2.926.006 ₫
3.428.111 ₫ total
22 Aug - 23 Aug
includes taxes & fees
8.6/10 Excellent! (1,940 reviews)
"Ok"

Reviewed on 19 Aug 2025

Courtyard by Marriott Portland City Center
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 2.723.395 ₫ per night from 1 Sept to 2 Sept
2.723.395 ₫
3.174.116 ₫ total
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,710 reviews)
"My boyfriend and I stayed for our anniversary and we had a great time. It’s very clean, the beds are very comfortable, and everyone that works there is very pleasant. When we arrived for check in the person that helped us upgraded our room when he found out it was our anniversary. Everything in this ..."

Reviewed on 18 Aug 2025

The Paramount Hotel
See all 2,764 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.

Popular places to visit

Oregon Convention Center

Oregon Convention Center

5/5(1 review)

During your trip, find out what's happening in Oregon Convention Center, a top convention centre in Portland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Oregon Convention Center
Oregon Health and Science University

Oregon Health and Science University

5/5(1 review)

Walk around the campus at Oregon Health and Science University during your stay in Portland. Discover the area's shops or seek out its cycling trails.

Oregon Health and Science University
Portland State University

Portland State University

4/5(1 review)

Walk around the campus at Portland State University during your stay in Portland. Discover the acclaimed theatre scene in this vibrant area or seek out the cycling trails.

Portland State University

Frequently asked questions

How much does a Milwaukie holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday 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 holidays 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 neighbourhoods 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 holiday package to Milwaukie?
Whether you'd like to explore top attractions like Waverley Country Club and North Clackamas Aquatic Park on your Milwaukie holiday, 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 holiday 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 holiday package well in advance.
Is it cheaper to book a Milwaukie holiday as a package?
Expedia holiday 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 holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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 travelling 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 favourite season will help you decide when to get away.
  2. Budget wisely: Besides the price of your accommodation, 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 accommodation: After you've settled on your trip dates and duration, lock in the ideal Milwaukie holiday package for you.