Hillside Vacations from $371

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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.
Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Downtown Portland
Price was $563, price is now $371 per person
$371
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Portland (PDX)
9.2/10 Wonderful! (1,734 reviews)
Overall great location, friendly staff, the bed was top tier!!

Reviewed on Oct 13, 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 $976, price is now $631 per person
$631
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Portland (PDX)
9/10 Wonderful! (1,002 reviews)
Great hotel! The snacks with sensors were super frustrating, I would much rather have the fridge to put my own things than drinks that trigger a sensor and charge me when I move them around. This caused me to have to walk down to the check in to sort it out, they still didn’t take the charges off and I had to call when I got home to remove them. Otherwise this is a very nice spot to stay in Portland!

Reviewed on Oct 3, 2025

Holman Riverfront Park Hotel Salem, Tapestry by Hilton

Holman Riverfront Park Hotel Salem, Tapestry by Hilton

3.5 out of 5
Central Area
Price was $849, price is now $582 per person
$582
per person
Dec 22 - Dec 27
found 17 hours ago
Roundtrip non-stop flight included
Orange County (SNA) to Portland (PDX)
9/10 Wonderful! (347 reviews)
The bed was very comfortable, the whole place is well maintained and clean. The restaurant part of it makes excellent home made pasta. The only negative was that the building could get a little noisy - but not a huge deal and not really the hotel's fault

Reviewed on Oct 13, 2025

Grey Oak by Avantstay Coastal Charm, Near Beach & Golf

Grey Oak by Avantstay Coastal Charm, Near Beach & Golf

3 out of 5
Save 100% on your flight
Price was $2,934, price is now $2,103 per person
$2,103
per person
Dec 28 - Jan 3
found 14 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Portland (PDX)
10/10 Exceptional! (2 reviews)
Clean quiet and able to walk to the beach

Reviewed on Aug 16, 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

Holiday Inn Airport - Portland by IHG

Holiday Inn Airport - Portland by IHG

3 out of 5
8439 Ne Columbia Blvd, Portland, OR
Fully refundable
$67 nightly
The price is $78 total per night from Nov 2 to Nov 3
$78 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (2,675 reviews)
"Quick shuttle ride was nice after a late flight. Holiday Inn was fantastic."

Reviewed on Oct 12, 2025

Holiday Inn Airport - Portland by IHG
Courtyard by Marriott Portland City Center

Courtyard by Marriott Portland City Center

3.5 out of 5
550 SW Oak Street, Portland, OR
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $118 total per night from Oct 21 to Oct 22
$118 total
Oct 21 - Oct 22
Total with taxes and fees
8.6/10 Excellent! (2,128 reviews)
"Great space and price for a short stay"

Reviewed on Oct 12, 2025

Courtyard by Marriott Portland City Center
The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St, Portland, OR
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $114 total per night from Nov 2 to Nov 3
$114 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (2,886 reviews)
"The hotel was wonderfully clean, staff was very friendly and the overall stay was fantastic."

Reviewed on Oct 12, 2025

The Paramount Hotel
See all 2,755 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

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: 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
Portland: Willamette River 2.5-hour Dinner Cruise

Portland: Willamette River 2.5-hour Dinner Cruise

$127
per adult
96% of travellers recommend
Portland: Willamette River 2.5-hour Dinner Cruise
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.