A calm lake with reflections of houses and trees, surrounded by a forested area and a cloudy sky.

Milwaukie Vacations from $418

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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.
  • Jan 29 - Feb 1

    Mark Spencer Hotel + Flight

    Downtown Portland
    3 nights
    3.0 star property
    9.2/10 - Wonderful (2,554 reviews)
    "Quick check in, nice staff, everything was good."
    Reviewed November 11, 2026
    Roundtrip • Burbank (BUR) - Portland (PDX)
    BUR - PDX • Nonstop PDX - BUR • Nonstop
    $585
    $418
    per traveler
    found 1 day ago
    Mark Spencer Hotel
  • Jan 21 - Jan 24

    The Ritz-Carlton, Portland + Flight

    Downtown Portland
    3 nights
    5.0 star property
    9.4/10 - Exceptional (373 reviews)
    "Staff was wonderful and very helpful. Nice atmosphere throughout."
    Reviewed November 7, 2026
    Roundtrip • Los Angeles (LAX) - Portland (PDX)
    LAX - PDX • Nonstop PDX - LAX • Nonstop
    $1,087
    $706
    per traveler
    found 15 hours ago
    The Ritz-Carlton, Portland
  • Jan 21 - Jan 25

    Portland's White House + Flight

    Northeast Portland
    4 nights
    3.0 star property
    8.0/10 - Very good (2 reviews)
    "The property was absolutely gorgeous. We would give 5 stars all the way around, except there really was no staff or amenities. There were several times we would have like to speak with staff regarding locations, food or if there had been some extras offered we might have stayed on property. All in all the home is absolutely gorgeous!"
    Reviewed October 27, 2026
    Roundtrip • Houston (HOU) - Portland (PDX)
    IAH - PDX • 1 stop PDX - IAH • 1 stop
    $980
    $647
    per traveler
    found 1 day ago
    Portland's White House
  • Dec 25 - Dec 29

    Skamania Lodge + Flight

    Stevenson
    4 nights
    3.5 star property
    9.2/10 - Wonderful (1,091 reviews)
    Roundtrip • Dallas (DFW) - Portland (PDX)
    DFW - PDX • Nonstop PDX - DFW • 1 stop
    $1,042
    $782
    per traveler
    found 14 hours ago
    Skamania Lodge
  • Jan 26 - Jan 30

    Chapman Cove by Avantstay Gorgeous Beach Bungalow w/ Sauna + Flight

    Cannon Beach
    4 nights
    3.0 star property
    Roundtrip • Dallas (DFW) - Portland (PDX)
    DFW - PDX • Nonstop PDX - DFW • Nonstop
    Save 100% on your flight
    $1,799
    $1,358
    per traveler
    found 1 day ago
    Chapman Cove by Avantstay Gorgeous Beach Bungalow w/ Sauna

Where to stay in Milwaukie

Discover the charm of historic Milwaukie, where family-friendly vibes and outdoor adventures await. Explore downtown Milwaukie for local culture, or unwind at Oregon's best hotels. This area offers a perfect getaway for those seeking a blend of relaxation and exploration.

Portland

For travelers seeking a vibrant urban experience, Portland is the ultimate neighborhood for those who appreciate a blend of adventure and culture. With attractions like the Oregon Convention Center for events, the scenic Portland State University, and the exciting Veterans Memorial Coliseum for arena entertainment, there's something for everyone. Located within the city of Milwaukie, Portland offers easy access to these highlights, making it a smart choice for your vacation stay.

Forest Highlands

Experience the charm of Forest Highlands, an excellent hub for travelers eager to explore the vibrant city life and outdoor adventures that Portland has to offer. Just a mile from Milwaukie, this neighborhood provides easy access to attractions like the educational setting of Lewis and Clark College, the serene Tom McCall Waterfront Park, and the fascinating Oregon Museum of Science and Industry. With its appealing blend of business and leisure opportunities, Forest Highlands is a smart choice for your stay.

Oak Grove

If you are a family-oriented traveler, make the most of your visit by staying in Oak Grove, a haven for outdoor enthusiasts and nature lovers. This charming neighborhood offers easy access to Lewis and Clark College for educational pursuits, the scenic Tom McCall Waterfront Park for relaxation, and the Oregon Museum of Science and Industry for engaging experiences. Located around Milwaukie, Oak Grove provides a smart choice for budget-friendly accommodations while keeping you close to vibrant city life and beautiful landscapes.

Southgate

Immerse yourself in Southgate, where travelers seeking a blend of business, family, and outdoor experiences can easily access attractions like Portland State University, Tom McCall Waterfront Park, and the Oregon Museum of Science and Industry. This vibrant neighborhood around Milwaukie offers a variety of shopping and educational opportunities, making it an ideal base for exploring the area. Choosing Southgate for your stay ensures a well-rounded experience in the heart of Oregon.

Oatfield

Travelers seeking family-friendly options will find Oatfield an inviting neighborhood around Milwaukie, Oregon, offering easy access to vibrant attractions like the Oregon Museum of Science and Industry and the scenic Tom McCall Waterfront Park. With a mix of nature and urban experiences, Oatfield is perfect for those looking to enjoy local shopping and events. Its proximity to major venues makes it a smart choice for both leisure and business stays, ensuring a delightful visit for all.

Discover the most popular places to visit in Milwaukie

What to do in Milwaukie

Milwaukie Hotel Deals

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.

Frequently Asked Questions

How much does a Milwaukie vacation package cost?

Offering excellent value package deals from $418 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.