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

Milwaukie Vacations from $297

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The Latest Milwaukie Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Oct 4 - Oct 9

    Milwaukie Inn Portland South + Flight

    Oak Grove
    5 nights
    2.0 star property
    7.4/10 - Good (570 reviews)
    "What the treatment type of places is this that I checked into? Never been treated so poorly as a customer or guest after five nights of paid service. I was not accused nor warned a single time of an infraction leaving the behavior unprovoked, innapropriate, and honestly quite a disgusting and deplorable way to confront and treat in DV booking and then to continue to accept funds from the domestic violence grants that women are granted if they qualify, only to treat a single female, with the..."
    Reviewed July 24, 2026
    Roundtrip Denver (DEN) - Portland (PDX)
    DEN - PDXNonstop PDX - DENNonstop
    $427
    $297
    per traveler
    found 1 day ago
    Milwaukie Inn Portland South
  • Sep 17 - Sep 21

    Coast River Inn by OYO Seaside + Flight

    Seaside
    4 nights
    2.0 star property
    8.4/10 - Very Good (1,067 reviews)
    Roundtrip Denver (DEN) - Portland (PDX)
    DEN - PDXNonstop PDX - DENNonstop
    Save 100% on your flight
    $750
    $507
    per traveler
    found 1 day ago
    Coast River Inn by OYO Seaside
  • Sep 17 - Sep 21

    City Centre Motel by OYO + Flight

    Seaside
    4 nights
    2.0 star property
    7.0/10 - Good (1,003 reviews)
    "This place was a dump. The check in was down the street and parking was horrible. We got there and it was the very apparent that our room was where the old check in counter and workers stayed. They had refurbished it into a two bedroom apartment looking room and the place reeked of weed, because the other hotel guests just left their doors open and did not care, even though it was labeled as a smoke free zone. We did not feel safe, and we decided to go to another hotel. I do not recommend this..."
    Reviewed July 25, 2026
    Roundtrip Denver (DEN) - Portland (PDX)
    DEN - PDXNonstop PDX - DENNonstop
    Save 100% on your flight
    $714
    $484
    per traveler
    found 1 day ago
    City Centre Motel by OYO
  • Sep 17 - Sep 22

    The Nines, a Luxury Collection Hotel, Portland + Flight

    Downtown Portland
    5 nights
    5.0 star property
    9.2/10 - Wonderful (1,005 reviews)
    "Fantastic location and friendly staff."
    Reviewed July 27, 2026
    Roundtrip Burbank (BUR) - Portland (PDX)
    BUR - PDXNonstop PDX - BURNonstop
    Save 100% on your flight
    $924
    $640
    per traveler
    found 1 day ago
    The Nines, a Luxury Collection Hotel, Portland
  • Sep 17 - Sep 22

    Heathman Hotel + Flight

    Downtown Portland
    5 nights
    4.5 star property
    9.2/10 - Wonderful (1,021 reviews)
    "My favorite hotel ever. Boutique charm and personality, with amazing bonus amenities: The library--books really are signed by the authors, and not just a few! The fitness room--includes a heavy bag AND speed bag AND Mirror with lululemon studio app. It was lovely to stay in a place that felt one-of-a-kind, with history, and yet not need to compromise any comforts."
    Reviewed July 27, 2026
    Roundtrip Burbank (BUR) - Portland (PDX)
    BUR - PDXNonstop PDX - BURNonstop
    Save 100% on your flight
    $834
    $590
    per traveler
    found 1 day ago
    Heathman Hotel

Where to stay in Milwaukie

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

Oak Grove

Oak Grove offers a peaceful suburban retreat just outside Portland's urban bustle. This welcoming neighborhood boasts tree-lined streets and friendly locals. The historic Trolley Trail provides perfect paths for cyclists and walkers. Family-friendly Risley Park features playgrounds and green spaces for afternoon picnics. Budget-conscious travelers appreciate the affordable dining options and lodging compared to downtown Portland. The Willamette River is just a short drive away.

Southgate

Southgate offers a quiet suburban retreat just outside Portland with family-friendly parks and tree-lined streets. The neighborhood centers around Southgate Park where locals gather for weekend picnics under mature oak trees. Shopping enthusiasts will appreciate easy access to Clackamas Town Center and Clackamas Promenade. Two convenient metro stations connect you to downtown Portland in minutes. Expect authentic middle-class American neighborhood life with modest homes and well-kept lawns. While dining options are limited locally, nearby Milwaukie downtown provides more choices for evening entertainment and diverse cuisine.

Oatfield

This peaceful Portland suburb offers a genuine slice of American residential life away from tourist crowds. Oatfield charms visitors with tree-lined streets and well-kept family homes. The neighborhood centers around North Clackamas Park with its expansive green spaces and recreational facilities. Travelers appreciate Oatfield's quiet atmosphere and affordability compared to downtown Portland. The area provides convenient access to nearby attractions like North Clackamas Aquatic Park and Clackamas Town Center. Though dining options are limited, the authentic suburban experience makes this a perfect base for exploring the greater Portland region.

Ardenwald

Ardenwald offers a peaceful retreat in Milwaukie with tree-lined streets and charming single-family homes. This residential haven provides an authentic local experience away from Portland's bustling core. Johnson Creek meanders through the neighborhood, creating natural beauty alongside Ardenwald Park's walking paths and playground. The SE Tacoma/Johnson Creek Station connects you to Portland while maintaining the area's tranquil atmosphere. Morning bird songs and gentle creek sounds create a soothing backdrop for walks under mature Douglas firs and maples. Visitors appreciate this quiet enclave for its genuine neighborhood feel and access to nature.

Jennings Lodge

Jennings Lodge offers a tranquil retreat from Portland's urban energy, with tree-lined streets and peaceful residential charm. The Willamette River flows nearby, providing scenic walking paths and nature observation spots for outdoor enthusiasts. This welcoming community feels authentically suburban with its well-kept homes and gardens. The neighborhood provides affordable accommodation options compared to downtown Portland. Local cafes and small eateries dot the area, though dining choices are limited. A car is recommended for exploring beyond Jennings Lodge, as public transit connections to Portland are infrequent.

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 $297 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.