McMenamins Kennedy School

Set on the edge of Portland’s slightly raffish but endearingly funky Alberta Arts District, this 35-room property occupies a former elementary school built in 1915. A project of the much-loved McMenamins company—which has converted many disused and dreary Portland buildings into convivial pubs and quirky hotels—the hotel has retained many design elements from its former life. Many of the guest rooms (all of which have tall windows that flood the rooms with light) have original chalkboards on the walls and roomy closets fashioned out of former cloakrooms. Room rates include Wi-Fi, parking, and admission to the on-site movie theater (formerly the school auditorium). Depending on your mood (or reputation), you can order a house-brewed ale in either the Detention Bar or the Honors Bar; or go for a burger in the casual Courtyard Restaurant (once the cafeteria). The one drawback (or plus, if you’re nostalgic) is that faintly musty smell that may transport you back to your own grade-school years.

Tip: Bring your swimsuit and plan for a dip in the hotel’s ceramic-tiled pool, on the former site of the old teachers’ lounge.

Room to Book: All the rooms are similar in size and appearance, but the Cherry Tree Room stands out for its view of a stately cherry tree that flowers beautifully each spring.