Milwaukie Vacations from $395

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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.

The Latest Milwaukie vacation packages

Price found within the past 48 hours. Click for updated prices.
Two Capes Lookout

Two Capes Lookout

2 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PDX)
10/10 Exceptional! (31 reviews)
Lindsey at the property was wonderful to our family, we were celebrating our boys birthdays and took them to ride quads at sandlake. Stayed here after and they were over the moon. We had a great comfy dome, lovely fire pit, s’mores delivered to us and blankets to keep us warm around the fire. We couldn’t be more pleased with our experience at two capes.

Reviewed on Aug 1, 2025

Sentinel Hotel

Sentinel Hotel

5 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 31 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PDX)
8.8/10 Excellent! (1,001 reviews)
Beautiful older property, good closet space. Only negative are the toilets are very low unless in a handicapped room if you have issue squatting

Reviewed on Jul 28, 2025

Skamania Lodge

Skamania Lodge

3.5 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 26
found 5 hours ago
Roundtrip flight included
Phoenix (PHX) to Portland (PDX)
8.8/10 Excellent! (1,010 reviews)
Water was turned off

Reviewed on Jul 24, 2025

Clackamas Inn & Suites

Clackamas Inn & Suites

2.5 out of 5
per person
Aug 31 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PDX)
7.6/10 Good! (1,015 reviews)
We are in a room right next to the eievator and hear nothing in the room. We pull a teardrop trailer and have no issue parking with it.

Reviewed on Jul 19, 2025

Holiday Inn: Portland- I-5 S (Wilsonville) by IHG

Holiday Inn: Portland- I-5 S (Wilsonville) by IHG

3 out of 5
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Portland (PDX)
8/10 Very Good! (862 reviews)
The room looked like it hadn’t been cleaned prior to us. There was hair in the shower and crumbs/dirt in the bathroom. The bed was very comfortable and the sheets were clean

Reviewed on Jul 17, 2025

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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

Discover the most popular places to visit in Milwaukie

Moda Center

Moda Center

See sporting teams do battle and rock out to musical legends at one of Portland’s major venues for sports and big-ticket entertainment events.

Moda Center
Oregon Convention Center

Oregon Convention Center

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

Oregon Convention Center
Oregon Zoo featuring zoo animals and landscape views as well as a large group of people

Oregon Zoo

Awesome beasts native to America have a home alongside exotic and endangered species from around the world at this picturesque Portland attraction.

Oregon Zoo

What to do in Milwaukie

Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-hour Lunch Cruise on the Willamette River

$87
per adult
98% of travellers recommend
Portland: 2-hour Lunch Cruise on the Willamette River
Half-Day Multnomah Falls & Gorge Waterfalls Tour

Half-Day Multnomah Falls & Gorge Waterfalls Tour

$85
per traveler
96% of travellers recommend
Half-Day Multnomah Falls & Gorge Waterfalls Tour
Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

$7
per adult
Downtown Golden Adventure Quest Experience in Portland
See all activities in Milwaukie

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 refundableReserve now, pay when you stay
$119 nightly
The price is $138 total per night from Aug 10 to Aug 11
$138 total
Aug 10 - Aug 11
Total includes taxes and fees
8.6/10 Excellent! (1,879 reviews)
"Very convenient location"

Reviewed on Aug 1, 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
$108 nightly
The price is $125 total per night from Sep 1 to Sep 2
$125 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (2,645 reviews)
"I liked the location and how welcoming the staff was when we had checked in. There was a lot to do around the hotel and the hotel also had a nice restaurant and bar."

Reviewed on Jul 31, 2025

The Paramount Hotel
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
$91 nightly
The price is $105 total per night from Aug 6 to Aug 7
$105 total
Aug 6 - Aug 7
Total includes taxes and fees
7.6/10 Good! (2,472 reviews)
"Inexpensive and close to airrport."

Reviewed on Jul 31, 2025

Red Lion Hotel Portland Airport
See all 2,799 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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Frequently asked questions

How much does a Milwaukie vacation package cost?
Offering excellent value package deals from $395 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?
December, January and February are great times to search for cheap Milwaukie vacation packages. Traveling in less busy months means you can generally find better prices on accommodations and flights.
How many days is enough for Milwaukie?
We suggest planning a Milwaukie vacation for around 2 days. This will give you plenty of time to check off top attractions including North Clackamas Aquatic Park and Milwaukie Farmers Market, as well as check out neighborhoods like Downtown Portland and Lloyd District. You might even be able to slot in a day trip (or two) outside of Milwaukie.
Is it worth booking a vacation package to Milwaukie?
Whether you'd like to visit attractions 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?
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. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to visit Milwaukie.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you should factor in other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Milwaukie.
  3. Use our trip planning tool to explore Milwaukie: Research every part of your trip to Milwaukie with this handy planner. Invite your friends and family to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you know more about Milwaukie, you can figure out the right length of your vacation. Put together a draft plan and give yourself enough time to cover everything you want to see.
  5. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, book the perfect Milwaukie vacation package for you.
  6. Book any excursions or activities: Now to the fun part — organizing everything you want to see and do. Check out some of the exciting things to do in Milwaukie and reserve your tickets early to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Milwaukie vacation packages?
Your Milwaukie trip should be a relaxing escape from your daily routine, not a source of money worries. So to allow you more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden 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.