Hillside Vacations from $321

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Your Hillside Vacation

The easiest way to experience this unique city is with a customized Hillside vacation package. Stay in the neighborhood of Overlook, which is good for cycling, bars and pubs and dining or choose someplace else — our packages are all about you. Eager to explore your new surroundings? Oregon Zoo, Portland State University and Portland Japanese Garden are just a few of the top places to visit during your trip to Hillside. Whatever your travel plans or budget, putting together the ultimate tailored Hillside vacation is simple with Expedia.

The Latest Hillside Vacation Packages

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

Hotel Lucia

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $506, price is now $321 per person
$321
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Portland (PDX)
9.2/10 Wonderful! (1,222 reviews)
The hotel was artsy & clean. Lloyd at the front desk was very genuine & pleasant (not fake hospitality-nice). Downtown can have some very unpleasant but unavoidable smells (especially in summertime) so I really appreciated the nice fragrance they have going throughout the lobby and halls. Bathroom was a bit cramped and odd but I'm used to living in small, older buildings so it wasn't a huge deal. If it's in the budget on our next visit we'll be staying here again.

Reviewed on Sep 2, 2025

Two Capes Lookout

Two Capes Lookout

2 out of 5
Save 100% on your flight
Price was $794, price is now $431 per person
$431
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
9.8/10 Exceptional! (59 reviews)
Beautiful well appointed cabins with excellent views of the ocean and surrounding forest on clear days. Our cabin was cozy with limited room. However they are comfortable considering the limited square footage.

Reviewed on Sep 2, 2025

Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Downtown Portland
Save 100% on your flight
Price was $680, price is now $385 per person
$385
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Portland (PDX)
9.2/10 Wonderful! (1,686 reviews)
The staff were amazing! From the moment I checked in the front desk was amazing. They made sure to accommodate us right away. They are fast with finding solutions we had a minor inconvenience and they resolved it better than I could imagine. And I also received many good recommendations for places to visit as it was our first time visiting Portland. I couldn’t have asked for a better place to stay the room was clean to the T the bed was super comfy and I loved the bedroom aesthetic 💗 Soso happy!

Reviewed on Sep 3, 2025

Hotel deLuxe

Hotel deLuxe

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $496, price is now $324 per person
$324
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Portland (PDX)
8.6/10 Excellent! (1,006 reviews)
Location, amenities, and parking were great!

Reviewed on Sep 3, 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 $773, price is now $523 per person
$523
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop 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

Where to stay in Hillside

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

Hillside 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 2,711 properties in Hillside
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 Hillside

Pittock Mansion showing a house, a garden and a monument

Pittock Mansion

A wonderfully preserved example of life in a bygone era and spectacular views await at one of America’s finest stately homes.

Pittock Mansion
👔✨✨🌙

Hillside Park Community Center

Hillside Park Community Center is just one of the places to see in Portland, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or visit the shops in the area.

Hillside Park Community Center
Moda Center

Moda Center

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

Things to do

We'll take you to sites on both sides of the river on this City of Portland guided shuttle tour

Portland City Tour: Views and News (Our Best Selling Tour!)

$79
per adult
100% of travellers recommend
Portland City Tour: Views and News (Our Best Selling Tour!)
Welcome to Portland! TripAdvisor 'Hall of Fame' tours by talented local guides. 'Certified Excellent' every year since 2010!

'The Best of Portland' City Tour: Small-Group Sightseeing Tour

$102
per adult
'The Best of Portland' City Tour: Small-Group Sightseeing Tour
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
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.