Milwaukie Vacation Packages

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Your Milwaukie Vacation

Reserve a Milwaukie vacation package and focus on what counts — enjoying yourself. This means no more planning stresses, just lots more time to immerse yourself in the delights of this fascinating city, such as its rich history and spectacular views. Fill up your itinerary with visits to Oregon Zoo, Portland State University and Portland Japanese Garden, some of the things you just have to see during your trip to Milwaukie. Don't put off visiting this city any longer. Your perfect Milwaukie vacation is just a few clicks away with Expedia.

Top Milwaukie Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Washington Plaza Apartments

Washington Plaza Apartments

3 out of 5
Downtown Portland
Price was CA $959, price is now CA $704 per person
CA $704
per person
Aug 16 - Aug 22
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PDX)
8.2/10 Very good! (417 reviews)
Great location. Easy check in, clean room with everything we needed. Comfortable bed

Reviewed on Jul 11, 2026

The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

5 out of 5
Downtown Portland
Price was CA $1,642, price is now CA $1,112 per person
CA $1,112
per person
Aug 16 - Aug 22
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PDX)
9.2/10 Wonderful! (1,001 reviews)
Phenomenal service. Beautiful, clean & well maintained property. Excellent restaurants. 10 out of 10 will go again.

Reviewed on Jul 12, 2026

Hilton Vancouver Washington

Hilton Vancouver Washington

3.5 out of 5
Downtown Vancouver
Price was CA $1,272, price is now CA $938 per person
CA $938
per person
Aug 16 - Aug 20
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
9/10 Wonderful! (1,001 reviews)
.

Reviewed on Jul 13, 2026

The Ashley Inn & Suites

The Ashley Inn & Suites

2.5 out of 5
Wecoma Beach
Price was CA $999, price is now CA $770 per person
CA $770
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.2/10 Very good! (2,685 reviews)
Pretty good place to spend the night.

Reviewed on Jul 14, 2026

WorldMark Portland - Waterfront Park

WorldMark Portland - Waterfront Park

2.5 out of 5
Downtown Portland
Price was CA $1,396, price is now CA $1,096 per person
CA $1,096
per person
Aug 16 - Aug 22
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PDX)
8.8/10 Excellent! (68 reviews)
Beware the studios only have a pull out couch as a sleeping option. The bed is hard and a cement slab! The most uncomfortable sleeping option ever. I even tried to use the sofa cushions to make it bearable.....not a solution at all. See pic

Reviewed on May 5, 2026

Ready to book your vacation to Milwaukie?

 

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Milwaukie Hotel Deals

The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St Portland OR
The price is CA $151 per night from Aug 10 to Aug 11
CA $151
CA $176 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (3,545 reviews)
"The staff was great. Hotel and room was very clean."

Reviewed on Jul 14, 2026

The Paramount Hotel
The Duniway Portland A Hilton Hotel

The Duniway Portland A Hilton Hotel

4.5 out of 5
545 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 9 to Aug 10
CA $239
CA $277 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"Bad service and staff. Very rude"

Reviewed on Jul 10, 2026

The Duniway Portland A Hilton Hotel
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 CA $157 per night from Jul 19 to Jul 20
CA $157
CA $184 total
Jul 19 - Jul 20
includes taxes & fees
8.8/10 Excellent! (2,498 reviews)
"Very good staff and clean room. Location is good to walk to the pearl district, but if you are a solo female traveler, walking around this area might make you feel a little unsafe."

Reviewed on Jul 13, 2026

Courtyard by Marriott Portland City Center
See all 2,885 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.
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Stay near popular Milwaukie attractions

Clackamas Town Center with a Sprint store and a Starbucks.

Clackamas Town Center

8.6/10 (653 reviews)
During your trip to Happy Valley, you can find the perfect gifts to bring home at Clackamas Town Center. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

What to do in Milwaukie

Half-Day Multnomah Falls & Gorge Waterfalls Tour

Half-Day Multnomah Falls & Gorge Waterfalls Tour

CA $115
per traveller
96% of travellers recommend
Half-Day Multnomah Falls & Gorge Waterfalls Tour
Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-Hour Lunch Cruise Through Downtown

CA $125
per adult
98% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
Portland: Willamette River 2.5-hour Dinner Cruise

Portland: Dinner Cruise on the Willamette River

CA $183
per adult
96% of travellers recommend
Portland: Dinner Cruise on the Willamette River
See all activities in Milwaukie

Frequently asked questions

How much does a Milwaukie vacation package cost?
You'll find cheap prices from CA $704 on Expedia for your Milwaukie escape. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Milwaukie costs.
What are the cheapest months to go to Milwaukie?
January, February and April are great times to search for cheap Milwaukie vacation packages. Opting to travel in less busy months means you can usually find reduced prices on accommodations and flights.
How many days is enough for Milwaukie?
With about 2 days, you'll have plenty of time to enjoy popular neighbourhoods like Downtown Portland and Lloyd District during your Milwaukie vacation. Make sure to also add Portland Japanese Garden and Tom McCall Waterfront Park to your sightseeing itinerary. Looking for more adventures? Consider exploring outside of Milwaukie on tours and day trips.
Is it worth booking a vacation package to Milwaukie?
Whether you're looking to explore top sights like Waverley Country Club and North Clackamas Aquatic Park on your Milwaukie vacation, or coming for its great shopping, distilleries and craft breweries and bars and pubs, there's something for everyone here. With so much to experience, you'll soon discover why so many people think Milwaukie is a good vacation destination.
How to find the best Milwaukie package deals?
Begin your search for a Milwaukie package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," 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 Milwaukie package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Milwaukie escape off to a flying start.
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, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the freedom to create a personalized Milwaukie vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Milwaukie?
If you're planning an impromptu Milwaukie adventure, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Milwaukie?

  1. Choose when to get away: Check your diary and get your bags packed. Your preferred season and the activities on offer will also help you decide when to vacation in Milwaukie.
  2. Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and activities. Your hotel will probably be the largest expense during your trip to Milwaukie.
  3. Decide how long to go away for: Now that you're more familiar with Milwaukie, you can figure out the right length of your break. Create a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customized Milwaukie vacation package.

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