Hillside Vacation Packages

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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.

Bowline Hotel

CA $848

per person

Oct 23 - Oct 26

found 10 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Portland (PDX)

9.4/10 Exceptional! (1,005 reviews)

Kimpton Hotel Vintage Portland by IHG

Downtown Portland

CA $1,471

per person

Oct 3 - Oct 10

found 17 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PDX)

9/10 Wonderful! (1,000 reviews)

WorldMark Portland - Waterfront Park

Downtown Portland

CA $1,179

per person

Oct 3 - Oct 10

found 17 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PDX)

8.8/10 Excellent! (69 reviews)

Great location. It is a timeshare, so be prepared for the sales pitch

Reviewed on Aug 5, 2026

The Nines, a Luxury Collection Hotel, Portland

Downtown Portland

CA $1,140

per person

Nov 7 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Portland (PDX)

9.2/10 Wonderful! (1,007 reviews)

Very central to downtown and very well kept hotel. Friendly staff.

Reviewed on Aug 14, 2026

Heathman Hotel

Downtown Portland

CA $890

per person

Oct 7 - Oct 10

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Portland (PDX)

9.2/10 Wonderful! (1,033 reviews)

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

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.

A forested area with a stone structure, wooden benches, and a pathway leading to a central point.

Northeast Portland

1 out of top 10 points of interest in this area

Inner Northeast Portland boasts shopping areas like Lloyd District and Alberta Arts District, while the area near Burnside Bridge offers a lively nightlife with bars such as The Chesterfield and music venues like The Doug Fir Lounge.

A street with a modern building featuring large murals, parked cars, and a café with outdoor seating.

Pearl District

Discover art galleries like Elizabeth Leach Gallery, dine at diverse restaurants, and unwind in public plazas such as Jamison Square. Easily navigate with the Portland Streetcar and explore nearby iconic Powell's City of Books.

A dinosaur statue in front of a building with a glass facade and the letters 'OMS' on it.

Southeast Portland

1 out of top 10 points of interest in this area

Stretching from the Willamette River to Gresham, Southeast Portland boasts the scenic Mt. Tabor Park and the quirky Hawthorne district with its subculturally oriented shops. Don't miss exploring Reed College campus!

A cable car system, a cityscape with high-rise buildings, a river, and a mountain in the background.

Southwest Portland

2 out of top 10 points of interest in this area

Downtown Portland boasts cultural, educational, and retail hotspots, with attractions like Tom McCall Waterfront Park, Portland Art Museum, and Pioneer Place mall. Enjoy pedestrian-friendly streets and unique residential areas in Southwest Portland.

Hillside Hotel Deals

The Paramount Hotel

808 SW Taylor St Portland OR

Fully refundableReserve now, pay when you stay

CA $155

CA $181 total

Aug 23 - Aug 24

includes taxes & fees

9.2/10 Wonderful! (3,604 reviews)

"Second time staying here! Great central stay for downtown Portland. Close to several parking garages."

Reviewed on Aug 14, 2026

Oxford Suites Portland - Jantzen Beach

12226 N JANTZEN DRIVE Portland OR

Fully refundableReserve now, pay when you stay

CA $130

CA $167 total

Aug 23 - Aug 24

includes taxes & fees

Hyatt Regency Portland at the Oregon Convention Center

375 NE Holladay St Portland OR

Fully refundableReserve now, pay when you stay

CA $176

CA $244 total

Aug 30 - Aug 31

includes taxes & fees

9.4/10 Exceptional! (1,764 reviews)

"The location and rooms were great. Our shower leaked, but everything else was fine."

Reviewed on Aug 15, 2026

See all 2,846 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.

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 $848. 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

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.

See properties

Things to do

Half-Day Multnomah Falls & Gorge Waterfalls Tour

CA $114

per traveller

96% of travellers recommend

Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-Hour Lunch Cruise Through Downtown

CA $124

per adult

98% of travellers recommend

Full-Day Mount Hood & Multnomah Falls Tour

CA $188

per traveller

96% of travellers recommend

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.

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Hillside Vacation

Top Holiday Package Deals in Hillside

Bowline Hotel

Kimpton Hotel Vintage Portland by IHG

WorldMark Portland - Waterfront Park

The Nines, a Luxury Collection Hotel, Portland

Heathman Hotel

Where to stay in Hillside

Downtown Portland

Northeast Portland

Pearl District

Southeast Portland

Southwest Portland

Hillside Hotel Deals

The Paramount Hotel

Oxford Suites Portland - Jantzen Beach

Hyatt Regency Portland at the Oregon Convention Center

Frequently asked questions

Stay near popular Hillside attractions

Pittock Mansion

Hillside Park Community Center

Things to do

Half-Day Multnomah Falls & Gorge Waterfalls Tour

Portland: 2-Hour Lunch Cruise Through Downtown

Full-Day Mount Hood & Multnomah Falls Tour