Search Deals onMilwaukie Vacation Packages
Milwaukie Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
City Centre Motel by OYO
Save 100% on your flight
Price was $739, price is now $550 per person
$550
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Denver (DEN) to Portland (PDX)
Stay at this motel in Seaside. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions Seaside Beach and Ecola State Park are located nearby.
The Independence
Save 100% on your flight
Price was $1,012, price is now $725 per person
$725
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Portland (PDX)
Book a stay at this business-friendly hotel in Independence. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Independence Heritage Museum and Independence Public Library are located nearby.
Clean, pleasant, amazing beds and showers. Food and drinks were amazing at the restaurant as well. Will def stay here again if I’m in the area!
Reviewed on Aug 17, 2026
Four Bears by Avantstay Walk to Beach, Hot Tub, Ocean View
Save 100% on your flight
Price was $1,955, price is now $1,435 per person
$1,435
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Portland (PDX)
Book a stay at this business-friendly cottage in Arch Cape. Enjoy free parking, a beach locale, and patios. Popular attractions Haystack Rock and Cannon Beach are located nearby.
Royal Canoe by Avantstay Walk to the Shore + Cozy Fireplace
Save 100% on your flight
Price was $2,034, price is now $1,493 per person
$1,493
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Portland (PDX)
Stay at this cottage in Arch Cape. Enjoy free parking and balconies. Popular attractions Haystack Rock and Cannon Beach are located nearby.
Great location! Everything was clean and nice. We loved it!
Reviewed on Jul 22, 2026
Holiday Inn Express Newberg - Wine Country by IHG
Price was $905, price is now $669 per person
$669
per person
Nov 6 - Nov 13
found 7 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Portland (PDX)
Book a stay at this business-friendly hotel in Newberg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hoover-Minthorn House Museum and Jaquith Park are located nearby.
Skamania Lodge
Price was $826, price is now $611 per person
$611
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to Portland (PDX)
Book a stay at this spa resort in Stevenson. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Columbia Gorge Interpretive Center Museum and Skamania Lodge Golf Course are located nearby.
Was disappointed in the $15 parking fee. Understandable in urban environments, but seems opportunistic here. Bathroom door also was water damaged and falling a part at the bottom.
Reviewed on Aug 16, 2026
Sanctuary by the Sea by Avantstay Waterfront + Views
Save 100% on your flight
Price was $3,842, price is now $2,844 per person
$2,844
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Portland (PDX)
Stay at this cottage in Arch Cape. Enjoy free parking, a beach locale, and balconies. Popular attractions Haystack Rock and Cannon Beach are located nearby.
Beach Pines Bungalow by Avantstay Classic Cottage Steps to the Beach w/ Private Yard
Save 100% on your flight
Price was $1,798, price is now $1,332 per person
$1,332
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Portland (PDX)
Book a stay at this beach condo in Arch Cape. Enjoy free parking, a beach locale, and concierge services. Popular attractions Haystack Rock and Cannon Beach are located nearby.
We absolutely loved it. Can’t wait to go back!
Reviewed on Mar 23, 2026
Milwaukie Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Milwaukie Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Oct 12 - Mon, Oct 19
SFO
San Francisco Intl.
PDX
Portland Intl.
$119 Roundtrip, found 2 days ago
$119
Roundtrip
found 2 days ago
Sun, Oct 11 - Fri, Oct 23
LAX
Los Angeles Intl.
PDX
Portland Intl.
$120 Roundtrip, found 5 days ago
$120
Roundtrip
found 5 days ago
Thu, Dec 24 - Wed, Jan 6
SAN
San Diego Intl.
PDX
Portland Intl.
$137 Roundtrip, found 19 hours ago
$137
Roundtrip
found 19 hours ago
Tue, Sep 8 - Fri, Sep 18
DEN
Denver Intl.
PDX
Portland Intl.
$170 Roundtrip, found 6 days ago
$170
Roundtrip
found 6 days ago
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