Built in the 1970s, this groovy hotel has been restored to its former glory and now features funky rooms with bright colors, comfortable linens, private decks and a bevy of amenities. The artwork seen throughout is done by local artists and the rooftop terrace offers a great view. King and queen suites are available with full kitchens and wet bars. Although there is no on-site restaurant, the Inn at Northrup Station is conveniently located in a bustling neighborhood filled with a wide variety of food options. For a truly unique stay in Portland, this hotel lives up to the hype.

Just 10 minutes northeast of Downtown Portland, the McMenamin brothers have created yet another Portland treasure here. The 1915 Kennedy School was slated for demolition before the McMenamins intervened. Now a nostalgic retreat, each room features its own charming theme, complete with a chalkboard. Have a drink at the School Theater Bar and relish delicious pizza. Check out the expansive menu at the restaurant and later catch a movie. Peruse the original artwork adorning the hallways and tour the Concordia Brewery.