Hillside Vacations from $302
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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
Hood River Hotel
Reviewed on Aug 28, 2026
Where to stay in Hillside
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.
Hillside Hotel Deals
The Paramount Hotel
DoubleTree by Hilton Hotel Portland
"Very nice clean friendly place to stay. We will come again"
Reviewed on Sep 1, 2026
Country Inn & Suites by Radisson, Portland International Airport, OR
Stay near popular Hillside attractions
Pittock Mansion
Hillside Park Community Center
Things to do
Portland: 2-Hour Lunch Cruise Through Downtown
Portland: Dinner Cruise on the Willamette River
