Hillside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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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.

Top Holiday Package Deals in Hillside

Price found within the past 48 hours. Click for updated prices.
The Ashley Inn & Suites

The Ashley Inn & Suites

2.5 out of 5
Wecoma Beach
Price was CA $1,485, price is now CA $1,151 per person
CA $1,151
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PDX)
8.4/10 Very good! (2,683 reviews)
Microwave didn’t work… staff was awesome.

Reviewed on Jun 30, 2026

The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

5 out of 5
Downtown Portland
Price was CA $1,660, price is now CA $1,270 per person
CA $1,270
per person
Aug 3 - Aug 7
just found
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PDX)
9.2/10 Wonderful! (1,003 reviews)
It's a nice hotel but nowhere near luxury class and was overpriced. Paid almost 30 for a tiny piece of fish. Was told it came with peas when we asked what it came with. There were literally 12 peas. So I guess technically it came with peas. After eating the 4 bites of fish, we went out for dinner after dinner. Luxury prices but not a luxury experience.

Reviewed on Jun 27, 2026

Inn at Haystack Rock

Inn at Haystack Rock

2.5 out of 5
Downtown Cannon Beach
Price was CA $2,597, price is now CA $2,001 per person
CA $2,001
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PDX)
8.6/10 Excellent! (1,003 reviews)
Nice room!

Reviewed on Jun 30, 2026

SaltLine Hotel

SaltLine Hotel

3 out of 5
Price was CA $1,984, price is now CA $1,531 per person
CA $1,531
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PDX)
9.4/10 Exceptional! (1,080 reviews)
Friendly staff. Excellent location, close to the beach, retailers and entertainment. The hot tub pool was very welcome, as was the complimentary breakfast.

Reviewed on Jun 27, 2026

River Inn at Seaside

River Inn at Seaside

2.5 out of 5
Price was CA $1,902, price is now CA $1,496 per person
CA $1,496
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PDX)
9/10 Wonderful! (1,219 reviews)
Installations are getting a bit outdated and worn out

Reviewed on Jun 29, 2026

Where to stay in Hillside

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

Downtown Portland

4.5/5(557 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
The price is CA $159 per night from Jul 5 to Jul 6
CA $159
CA $185 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (3,503 reviews)
"Great location and service. Highly recommended."

Reviewed on Jun 30, 2026

The Paramount Hotel
Red Lion Hotel Portland Airport

Red Lion Hotel Portland Airport

3 out of 5
7101 NE 82nd Ave Portland OR
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Jul 12 to Jul 13
CA $139
CA $162 total
Jul 12 - Jul 13
includes taxes & fees
7.8/10 Good! (2,843 reviews)
"Super cozy beds & room was clean. The customer service is outstanding. Great place for a great price. I’d definitely stay here again"

Reviewed on Jun 30, 2026

Red Lion Hotel Portland Airport
Moxy Portland Downtown

Moxy Portland Downtown

3 out of 5
585 SW 10TH AVENUE Portland OR
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Jul 5 to Jul 6
CA $135
CA $157 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (1,461 reviews)
"They do have parking close by but I did not use it. They did have valet service and the valet were very personable and always smiling. Duncan, at the check-in, was AMAZING!! I stayed 5 nights/6 days and every evening when I came back from my adventures, he would ask how my day went and if I needed ..."

Reviewed on Jun 30, 2026

Moxy Portland Downtown
See all 2,844 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
Family Vacations
Family Vacations

Frequently asked questions

How much does a Hillside vacation package cost?
We make it simple to explore the world, with Hillside packages starting from as little as CA $1,151. You'll have the flexibility to combine your favorite airlines, hotels and car rental. For the ultimate escape, why not add a few tours and activities to your travel itinerary?
How do I get a cheap travel package to Hillside?
One of the easiest ways to save money (and time) is to combine your bookings with Expedia. Flights, hotels, activities and rental cars — we've got everything you need. Choose a combination that suits you and watch your savings pile up. Of course, a travel package is never one-size-fits-all. That's why we offer over 550 air carriers and 1,000,000 hotel options from all over the world, which lets you customize your Hillside vacation.
Where should I stay in Hillside?
Visitors come from all over the world to experience Oregon Zoo and Portland State University in Hillside. Book a room within walking distance of these must-see attractions and visit them whenever you want.
What are the top hotels in Hillside?
Get your vacation off to a flying start by reserving a room at Forested Quiet Retreat, Pet Friendly. It's one of most popular properties in Hillside. Another comfortable option is Spectacular Views, Single Level W.
How far in advance should I book my Hillside vacation?
To score cheap prices, book ASAP. Air carriers usually advertise flights, along with some of the lowest fares, nearly 12 months prior to departure. Hotels, activities and car rental should also be booked early to avoid disappointment. If you've decided on a last-minute getaway to Hillside, there are always lots of great deals to be had on Expedia. Book your escape today!
What does an Expedia Hillside travel package include?
Expedia has all you need to organize your Hillside getaway, but what goes into your package depends on you. Choose from any combination of rental cars, flights and hotels. In search of some activities to keep you busy? Once you've made your booking, you can add them too. No matter your budget, there's a deal to meet your needs.
What should I know before booking a Hillside travel package?
Whether it's relaxation or adventure you're after, a Hillside vacation package lets you plan your escape your way. Plus, you'll score great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Hillside Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Hillside vacation package?
If your vacation plans in Hillside have changed, it's comforting to know that it's possible to cancel your booking. If you made your booking in the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may charge a cancellation fee. To find out more, visit our Customer Service Portal.

Stay near popular Hillside attractions

Pittock Mansion

9.6/10 (12 reviews)
A wonderfully preserved example of life in a bygone era and spectacular views await at one of America’s finest stately homes.
See properties

Things to do

Half-Day Multnomah Falls & Gorge Waterfalls Tour

Half-Day Multnomah Falls & Gorge Waterfalls Tour

CA $111
per traveller
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 Through Downtown

CA $122
per adult
98% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
Full-Day Guided Oregon Coast Tour from Portland

Full-Day Guided Oregon Coast Tour from Portland

CA $192
per adult
100% of travellers recommend
Full-Day Guided Oregon Coast Tour from 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.