Sunnyside Vacations from $285

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Sunnyside Vacation

The hassle-free way to experience this interesting city is with a customized Sunnyside vacation package. Base yourself in the neighborhood of Mississippi District, which is good for shopping, nightlife and bars and pubs or go someplace else — our packages are all about you. Fill your days with tours of Clackamas Town Center, Sunnyside Road Trailhead and Park Mountain Lane Trailhead, some of the attractions you should see during a trip to Sunnyside. Don't delay visiting this city any longer. Your ultimate Sunnyside vacation is a few quick clicks away with Expedia.

The Latest Sunnyside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Milwaukie Inn Portland South

Milwaukie Inn Portland South

2 out of 5
Oak Grove
Save 100% on your flight
Price was $417, price is now $285 per person
$285
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Portland (PDX)
7.4/10 Good! (568 reviews)
Good inn

Reviewed on Aug 2, 2026

The Dundee - A Trace Hotel

The Dundee - A Trace Hotel

3.5 out of 5
Save 100% on your flight
Price was $683, price is now $445 per person
$445
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Denver (DEN) to Portland (PDX)
10/10 Exceptional! (42 reviews)
Convient to wine country

Reviewed on Aug 1, 2026

Capitol Hill Motel

Capitol Hill Motel

2.5 out of 5
Southwest Portland
Save 100% on your flight
Price was $498, price is now $342 per person
$342
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Portland (PDX)
9.2/10 Wonderful! (860 reviews)
We just wanted a convenient, economical place to stay for a couple of nights and this was perfect. It was clean, safe and the staff were very nice. Lots of restaurants nearby. This was easy access to downtown Portland and surrounding area-without staying downtown. No frills but perfect to lay your head at night.

Reviewed on Jul 27, 2026

Skamania Lodge

Skamania Lodge

3.5 out of 5
Price was $706, price is now $497 per person
$497
per person
Oct 8 - Oct 11
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Portland (PDX)
9.2/10 Wonderful! (1,020 reviews)
Staff was excellent. Dining options were very good. Breakfast buffet was delicious.

Reviewed on Aug 3, 2026

OYO Hotel St. Helens, OR

OYO Hotel St. Helens, OR

2 out of 5
Price was $943, price is now $670 per person
$670
per person
Oct 25 - Nov 1
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PDX)
6/10 (467 reviews)
Not a property I would stay at again

Reviewed on Jul 30, 2026

Where to stay in Sunnyside

Find the best Sunnyside areas and neighborhoods for the activities you enjoy most. Learn more about Sunnyside
Two people sitting on a blanket by a marina with boats docked in the background.

Downtown Portland

1 out of top 10 points of interest in this area

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

Sunnyside 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
$113 nightly
The price is $131 total per night from Aug 23 to Aug 24
$131 total
Aug 23 - Aug 24
Total with taxes and fees
The Paramount Hotel
Oxford Suites Portland - Jantzen Beach

Oxford Suites Portland - Jantzen Beach

3 out of 5
12226 N JANTZEN DRIVE Portland OR
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $132 total per night from Aug 4 to Aug 5
$132 total
Aug 4 - Aug 5
Total with taxes and fees
9/10 Wonderful! (1,637 reviews)
"Breakfast was really great! Free drinks were a nice perk. Parking was easy and secure to find, and the room was nice, clean, and comfortable. Thank You!"

Reviewed on Aug 3, 2026

Oxford Suites Portland - Jantzen Beach
The Duniway Portland A Hilton Hotel

The Duniway Portland A Hilton Hotel

4.5 out of 5
545 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $175 total per night from Aug 30 to Aug 31
$175 total
Aug 30 - Aug 31
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Great location with attached parking."

Reviewed on Aug 3, 2026

The Duniway Portland A Hilton Hotel
See all 2,723 properties in Sunnyside
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

Stay near popular Sunnyside attractions

Sunnyside Road Trailhead

7.0/10 (13 reviews)
You can take time to visit Sunnyside Road Trailhead during your travels to Clackamas. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
See properties

Things to do

Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-Hour Lunch Cruise Through Downtown

$88
per adult
98% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
Portland: Willamette River 2.5-hour Dinner Cruise

Portland: Dinner Cruise on the Willamette River

$129
per adult
96% of travellers recommend
Portland: Dinner Cruise on the Willamette River
Picture 11 for Activity Portland: Champagne Brunch Cruise on Willamette River

Portland: Brunch Cruise on Willamette River

$105
per adult
92% of travellers recommend
Portland: Brunch Cruise on Willamette River
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.