Welcome to the coolest detention you’ll ever serve! In Portland’s eclectic Northeast neighborhood, there’s a hotel that used to be a school, and it’s not just a clever name. McMenamins Kennedy School is a century-old elementary school that’s been transformed into a boutique hotel with a twist.
Guests don’t just sleep in former classrooms, they explore hallways lined with student art and vintage chalkboards. The vibe is playful, the decor is retro, and the experience is anything but ordinary.
Ready to sleep in a classroom, soak in a courtyard pool, and rack up straight A’s in charm? Stick around – this Portland hotel has earned more 5-star reviews than a valedictorian has gold stars.
1. A Time Capsule With A Twist
Originally opened in 1915, Kennedy School served Portland’s Concordia neighborhood for decades before closing in the 1970s. Instead of being demolished, it was lovingly restored and reopened in 1997 as part of the McMenamins family of historic properties.
The renovation preserved much of the original architecture, including hardwood floors, tall windows, and classroom layouts. Today, those same classrooms are cozy guest rooms, complete with chalkboards and vintage fixtures. The hallways still echo with the energy of students past, but now they’re filled with travelers snapping selfies and admiring murals.
The school’s old boiler room, gymnasium, and cafeteria have all been reimagined into public spaces. It’s a celebration of Portland’s quirky spirit and a tribute to adaptive reuse. You won’t find cookie-cutter hotel design here – every corner tells a story.
Even the stairwells are artfully decorated with nods to the building’s academic roots. It’s history you can sleep in, and it’s wildly popular with locals and tourists alike.
2. The Rooms Are Anything But Standard
Each guest room is uniquely designed, often incorporating elements from its former life as a classroom. Some rooms still have chalkboards, while others feature student lockers or original wood trim. The beds are plush, the lighting is warm, and the vibe is unmistakably Portland.
You won’t find sterile hotel furniture here – think vintage desks, funky lamps, and colorful quilts. The rooms vary in size, from cozy singles to spacious suites that once held dozens of students. There’s free Wi-Fi, of course, and modern bathrooms tucked into the old layouts.
Guests often comment on the quiet charm and the feeling of stepping back in time. It’s a mix of comfort and character that’s hard to replicate.
Whether you’re traveling solo or with a group, there’s a room that fits your style. And yes, you can request a room in the “Principal’s Office.” It’s all part of the fun.
3. The amenities Are As Playful As The Concept
McMenamins Kennedy School isn’t just a place to sleep; it’s a place to explore. There’s a saltwater soaking pool in the courtyard, open year-round and surrounded by lush greenery. The old auditorium now hosts nightly movies, complete with comfy seating and a full menu.
Guests can wander through the school’s hallways, discovering hidden art installations and historic plaques. There’s a gift shop filled with quirky souvenirs and local crafts. The property also hosts live music, seasonal events, and guided history tours.
Families love the open spaces and kid-friendly atmosphere. Couples enjoy the romantic nooks and creative date-night options. Even locals drop by for a dose of nostalgia and relaxation.
It’s a hotel that feels like a community hub. And yes, there’s plenty to do without ever leaving the building.
4. The Location Makes It Easy To Explore Portland
Situated in the Concordia neighborhood, Kennedy School is just a short walk from the Alberta Arts District. This area is known for its vibrant street art, indie boutiques, and locally owned cafes. Guests can stroll to nearby parks, browse bookstores, or catch live performances at neighborhood venues.
Public transit is accessible, and downtown Portland is just a short drive away. The hotel offers free parking, which is a rare perk in the city. It’s a great base for exploring both urban attractions and natural beauty.
From Powell’s Books to Forest Park, everything is within reach. The neighborhood itself is quiet, tree-lined, and full of character. It’s the kind of place where you’ll want to linger. And when you return to Kennedy School, it feels like coming home.
5. The Art Is Everywhere – And It’s Local
McMenamins properties are known for their commitment to art, and Kennedy School is no exception. Murals cover the walls, ceilings, and even the bathrooms. Many pieces were created by local artists and reflect Portland’s diverse culture and history.
There are whimsical portraits, surreal landscapes, and tributes to the school’s past. The art isn’t just decoration – it’s storytelling. Guests often spend hours wandering the halls, discovering new details in every corner. The hotel offers a self-guided art tour, complete with maps and descriptions. It’s a gallery experience wrapped in a hotel stay.
Even the light fixtures and furniture are chosen with artistic flair. It’s immersive, inspiring, and totally Portland.
6. The Reviews Speak For Themselves
On Tripadvisor, Kennedy School holds a 4.3-star rating with hundreds of enthusiastic reviews. Guests praise the unique concept, friendly staff, and nostalgic atmosphere. Reddit threads call it “the most Portland hotel ever,” and Yelp users rave about the soaking pool and movie theater.
Many reviewers mention the comfort of the rooms and the charm of the decor. Families appreciate the kid-friendly vibe, while couples love the romantic touches. The hotel has earned a Travelers’ Choice award, placing it in the top tier of Portland accommodations.
Visitors often say they’ll return again and again. It’s not just a place to stay – it’s a place to remember. And yes, even the “detention” gets five stars.
7. It’s Perfect For Events And Celebrations
Kennedy School hosts weddings, reunions, and corporate retreats in its repurposed spaces. The old gymnasium and library are now event venues with vintage charm. There’s catering available, plus plenty of breakout spaces for mingling.
Guests love the idea of celebrating in a former school, complete with chalkboards and lockers. The setting is both nostalgic and novel, making it ideal for memorable gatherings. There’s also a calendar full of public events, from concerts to seasonal festivals.
Locals often book the space for birthdays and anniversaries. It’s a venue that sparks conversation and creativity. And yes, there’s plenty of room for dancing.
8. Families And Solo Travelers Both Feel Welcome
Kennedy School is designed to be inclusive and accessible. The layout is easy to navigate, and the staff is known for being helpful and kind. There are ramps, elevators, and ADA-compliant rooms available. Solo travelers enjoy the quiet charm and artistic inspiration.
Families appreciate the open spaces and kid-friendly amenities. The hotel offers packages and seasonal deals to make stays more affordable. There’s a sense of community that makes everyone feel at home. Whether you’re visiting Portland for the first time or returning for a nostalgic stay, Kennedy School delivers. It’s a place where stories are made. And yes, you’ll want to tell yours.
9. Final Bell: This Hotel Deserves An A+
McMenamins Kennedy School isn’t just a clever concept – it’s a fully realized experience. From the historic architecture to the modern comforts, it blends past and present in unforgettable ways. The reviews are real, the charm is authentic, and the memories are lasting. It’s a hotel that invites you to explore, relax, and relive your school days with a smile.
Whether you’re soaking in the courtyard pool or watching a movie in the auditorium, every moment feels special. The staff is welcoming, the rooms are cozy, and the vibe is pure Portland. It’s not just a place to stay – it’s a destination.
So pack your bags, sharpen your pencils, and get ready for a stay that earns top marks. Kennedy School is in session, and you’re on the honor roll.
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