A large, historic building with a red-tiled roof and a well-maintained garden with various flowers.
Photo by BDM Traveling
Open Photo by BDM Traveling

Hillside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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 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.
  • Dec 18 - Dec 22

    Jupiter Hotel + Flight

    Southeast Portland
    4 nights
    3.5 star property
    8.4/10 - Very good (1,000 reviews)
    "Cutest hotel I absolutely loved the vibe!"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Portland (PDX)
    YYZ - PDX • 1 stop PDX - YYZ • 2 stops
    CA $1,080
    CA $981
    per traveller
    found 3 hours ago
    Jupiter Hotel
  • Dec 27 - Jan 2

    RiverPlace Hotel + Flight

    Downtown Portland
    6 nights
    4.5 star property
    9.2/10 - Wonderful (1,003 reviews)
    Roundtrip • Toronto (YTO) - Portland (PDX)
    YYZ - PDX • 2 stops PDX - YYZ • 2 stops
    CA $1,883
    CA $1,533
    per traveller
    found 1 day ago
    RiverPlace Hotel
  • Dec 27 - Jan 2

    The Nines, a Luxury Collection Hotel, Portland + Flight

    Downtown Portland
    6 nights
    5.0 star property
    9.2/10 - Wonderful (1,001 reviews)
    Roundtrip • Toronto (YTO) - Portland (PDX)
    YYZ - PDX • 2 stops PDX - YYZ • 2 stops
    CA $1,902
    CA $1,607
    per traveller
    found 1 day ago
    The Nines, a Luxury Collection Hotel, Portland
  • Dec 18 - Dec 22

    Skamania Lodge + Flight

    Stevenson
    4 nights
    3.5 star property
    9.2/10 - Wonderful (1,093 reviews)
    "Friendly"
    Reviewed November 12, 2026
    Roundtrip • Toronto (YYZ) - Portland (PDX)
    YYZ - SEA • Nonstop SEA - YYZ • 1 stop
    CA $1,590
    CA $1,344
    per traveller
    found 1 day ago
    Skamania Lodge
  • Dec 27 - Jan 2

    Staybridge Suites Hillsboro North by IHG + Flight

    Hillsboro
    6 nights
    3.0 star property
    8.8/10 - Excellent (394 reviews)
    "loved the free laundry"
    Reviewed November 4, 2026
    Roundtrip • Toronto (YTO) - Portland (PDX)
    YYZ - PDX • 2 stops PDX - YYZ • 2 stops
    CA $1,543
    CA $1,404
    per traveller
    found 1 day ago
    Staybridge Suites Hillsboro North by IHG

Where to stay in Hillside

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

Downtown Portland

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.

Northeast Portland

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.

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.

Southeast Portland

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!

Southwest Portland

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.

Discover the most popular places to visit in Hillside

What to do near Hillside

Hillside Hotel Deals

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 $981. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.