Historic Milwaukie Vacations from $361

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Your Historic Milwaukie Vacation

Let our Historic Milwaukie vacation packages take you to a destination where long-lasting memories are waiting to be made. While it's especially known for its golfing, there's plenty more to love about this neighborhood. Not sure what to do during your trip to Historic Milwaukie? Nearby attractions such as Waverley Country Club, Milwaukie Farmers Market and Milwaukie Museum are good places to start. No matter your travel plans or budget, booking your perfect Historic Milwaukie vacation is a cinch with Expedia.

The Latest Historic Milwaukie Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Downtown Portland
Save 100% on your flight
Price was $617, price is now $361 per person
$361
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
9.2/10 Wonderful! (1,686 reviews)
As usual the staff , the hotel , the room was perfect this is why I only stay at the Mark Spencer whenever I am in Portland !

Reviewed on Aug 30, 2025

Two Capes Lookout

Two Capes Lookout

2 out of 5
Save 100% on your flight
Price was $785, price is now $466 per person
$466
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
9.8/10 Exceptional! (59 reviews)
The views were amazing! Also, Zack was so welcoming and made us feel comfortable.

Reviewed on Aug 20, 2025

Skamania Lodge

Skamania Lodge

3.5 out of 5
Save 100% on your flight
Price was $603, price is now $384 per person
$384
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Portland (PDX)
8.8/10 Excellent! (1,007 reviews)
Great view of river and good meals

Reviewed on Aug 28, 2025

The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

5 out of 5
Downtown Portland
Save 100% on your flight
Price was $702, price is now $490 per person
$490
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
9/10 Wonderful! (1,004 reviews)
Beautiful property with very helpful staff. Rooftop dining & great breakfast too.

Reviewed on Aug 28, 2025

Sunset Cove by Avantstay Beachfront w/ Balcony!

Sunset Cove by Avantstay Beachfront w/ Balcony!

3.5 out of 5
Save 100% on your flight
Price was $1,704, price is now $1,196 per person
$1,196
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Portland (PDX)
No reviews

Where to stay in Historic Milwaukie

Find the best Historic Milwaukie areas and neighborhoods for the activities you enjoy most. Learn more about Historic Milwaukie
Downtown Portland - South Waterfront showing picnicing, boating and a bay or harbor

Downtown Portland

4.5/5(4,488 area reviews)

Explore the Portland Art Museum, Oregon Historical Society, and Tom McCall Waterfront Park in this central business district with high-rise buildings. Enjoy walkable streets, and easily access public transportation like MAX light rail and Portland Streetcar.

Find hotels in Downtown Portland

Historic Milwaukie Hotel Deals

The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St, Portland, OR
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $121 total per night from Sep 22 to Sep 23
$121 total
Sep 22 - Sep 23
Total with taxes and fees
The Paramount 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
$102 nightly
The price is $118 total per night from Sep 28 to Sep 29
$118 total
Sep 28 - Sep 29
Total with taxes and fees
Courtyard by Marriott Portland City Center
Holiday Inn Airport - Portland by IHG

Holiday Inn Airport - Portland by IHG

3 out of 5
8439 Ne Columbia Blvd, Portland, OR
Fully refundable
$90 nightly
The price is $104 total per night from Sep 28 to Sep 29
$104 total
Sep 28 - Sep 29
Total with taxes and fees
Holiday Inn Airport - Portland by IHG
See all 2,715 properties in Historic 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Historic Milwaukie

Moda Center

Moda Center

4.5/5(1,165 reviews)

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

4.5/5(569 reviews)

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

4.5/5(610 reviews)

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

Oregon Zoo

Things to do

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