8 Coolest Hotels in Portland That Reflect the Spirit of the City

Portland’s Pearl District is a gleaming beacon of hipster charm, from old warehouses repurposed as craft breweries and art studios to Powell’s City of Books—a bookstore so huge and labyrinthine you need a map to navigate it. An area this cool and artsy demands an equally hip hotel, and it has just that in McMenamins Crystal.

Each room in the flatiron-style building is inspired by an artist, group, or song that’s been performed at nearby Crystal Ballroom, which has echoed with music and dance since 1914. Lyrics from Wilson Pickett, James Brown, and the White Stripes are scrawled across colorful walls, while headboards bear portraits painted by local artists.

The hipness doesn’t end there, though. There’s nightly music at Al’s Den, an intimate room named after 1940s gambling overlord Al Winter, and a tucked-away speakeasy bar. Even the basement saltwater pool, its wobbly edges recalling waves of sound, oozes rock ‘n’ roll cool.

Hotel Deluxe wasn’t named lightly. This property, in downtown Portland’s Goose Hollow neighborhood, oozes classic luxury from every velvet drape and crystal chandelier. The lobby of the 1912 building glints with mirrors and burnished gold, while film stills are dotted around the walls. (You can’t miss the huge “Casablanca” image that greets you on arrival.)

It sets the stage for the main event: the rooms. The décor manages to be simultaneously breezy and opulent, combining soothing pastel tones with luxurious textures. Each one is gorgeous, but to really live the film star dream, book the Marlene Dietrich Suite, whose centerpiece is an enormous circular bed.

Like many of Portland’s best hotels, the Deluxe isn’t only for overnight guests. Portland locals and passersby can come along to regular pop-up cinema screenings and weekly lobby tastings of craft beer, Oregon wines, and seasonally focused small plates—one of the lovely touches that imbues the property with true community spirit.

Most hotel lobbies offer cozy spots for lounging, maybe a few desks for working, and probably somewhere to grab a drink. The Duniway Portland likes to do things a little differently, which only seems apt in this city. At first glance, the huge sofas, jewel-toned armchairs, and chic bar suggest this place might lean towards traditional.

Yet, depending on the night of the week, you’re likely to spot dead giveaways that this place is anything but. A resident tarot expert offers free readings on Thursdays, while Wednesday means free whiskey cocktails. The hotel often hosts artisan craft markets, or offers the chance to have your portrait sketched by a local artist.

Every detail is the result of the hotel being impeccably attuned to its surroundings. Its name pays homage to Abigail Scott Duniway, known as Oregon’s Mother of Equal Suffrage for her campaigning for women’s voting rights. The restaurant, helmed by celebrity chef Chris Cosentino, serves house-cured meats and dishes that speak to the heritage (and ingredients) of the region. That commitment to all things local continues in the serenely stylish rooms, with framed art and furniture crafted by Oregon artisans.

It can be easy being green. It can also, as the Sentinel Hotel proves, be exciting, stylish, and fun. From the beehives on the roof (which produce the honey stocked in the rooms’ honor bars) and a restaurant committed to sustainable produce, to complimentary bikes for guests’ use, this chic hotel operates with one eye fixed on the environment.

There’s no compromising on comfort: rooms are plush with cozy plaid throws and bespoke furniture. Stay in an executive room for the ultimate indulgence. These huge spaces have fireplaces and terraces, plus access to the Room at the End of the Hall, a library-like lounge stuffed with local snacks, as well as hot and cold drinks.

The Sentinel comes with a story, too. Several, in fact, as the hotel is actually two historic buildings combined—the 1909-opened Seward hotel, whose roof bears the sentinels that inspired the current property’s name, and Elks Lodge, where secret ceremonies were held in elegant ballrooms.

The Domaine Serene Wine Lounge, off the lobby, brings Oregon’s celebrated wine country into the downtown hotel. The label, whose winery is a Tuscan-inspired villa surrounded by the vine-striped slopes of the Willamette Valley, pours award-winning Pinot Noir and Chardonnay here. You can have a tasting (included for overnight guests) but you’ll probably end up buying a glass—or bottle.

You know you’re in good hands from the moment you step into the Heathman Hotel‘s reassuringly classic, dark-wood paneled lobby. Floor-to-ceiling bookshelves heave with first editions around parquet floors, marble desks, and the kind of chairs and sofas you could take a nap in.

You probably could, if you really wanted to. But I’d recommend booking a room for an even better sleep. Clever use of textures and materials give each room the feel of a serene sanctuary. There’s wood paneling behind beds with woolen throws (and your ideal mattress, selected from a menu), deep-soaking marble bathtubs, and rugs and lamps providing soft light and comfy spots to relax.

Other cool (and oh-so Portland) touches include free bike rentals, in-room pizza delivery, and fitness kits—with yoga mats, weights, and gym towel—delivered to your room.

Back in the lobby, staff wheel out bourbons, gins, and other specialty distillations for a daily Local Spirits Social—the perfect opportunity to share stories and tips with fellow guests and Portland residents who have decided to swing by.

The Nines is just a few steps from Pioneer Square and all the dining, craft beer, and nightlife of downtown Portland. But that may not matter too much, because this uber-chic sleep has not one but two of the city’s most highly-rated restaurants.

Departure fills fast with hotel guests and locals, who come for Asian-inspired dishes and some of the most inspiring views in town. Tables spill onto the plant-filled rooftop terrace, gazing across skyscrapers to the Willamette River and mountains beyond.

Urban Farmer, tucked in an inner courtyard, offers a different but equally appealing vibe. It’s a steakhouse, yes, but not in any typical sense. Light, bright wood accents, planters filled with decorative grass, and a menu of Oregon-raised beef and zingy salads give a real sense of place.

The hotel’s rooms are dressed-up to, well, the nines too. Think Tiffany blue, gilded touches, and luxurious textures of satin and velvet, all paying subtle homage to the 1909 building’s original incarnation as the flagship store for Meier & Frank.

McMenamins Kennedy School was indeed once a school, and the hotel revels in its roots. You won’t end up in detention (though running in the hallways isn’t encouraged). But you can sip craft beer in an old classroom that’s now home to a microbrewery, and watch a movie in the auditorium, repurposed as a cinema with plush seating on jewel-toned sofas and armchairs (a far cry from stiff-backed school chairs).

You might even catch a cool local band playing in the old gym—PE kit optional—or play drag queen bingo in the bar.

The 1915 Art Nouveaux school building has been sensitively restored to stay true to its original purpose, and always with a sense of fun. Some of the rooms were once classrooms (yes, you can fall asleep) and come with cute touches like old chalkboards and cloakrooms, now used for your clothes rather that a pile of kids’ coats.

Other rooms stick to the education theme with literary-inspired décor. My favorite is the Beverly Cleary room, which pays tribute to the Oregon-born author and her most famous creation, Ramona Quimby.

At first glance, the Jupiter Hotel might feel like the reserve of the achingly cool. Look more closely, though, and you quickly realize that pretension has no place within these art-filled walls. Wander through the lobby or take a seat on one of the patio area’s chunky wooden benches and you’ll see groups of friends with beanie hats, band T-shirts, and sleeve tattoos, couples dressed in Fifties gear, ready for a night out in the Pearl District, and suited and booted colleagues fresh from business meetings.

What was once an abandoned motel in a no-go area is now one of the city’s most vibrant hotels, and it manages to seamlessly combine Golden Age glamour with unmistakable Portland vibes, from rowdy concerts in a dive-y bar that also serves chic cocktails to plush rooms with gilded lampshades and rock ‘n’ roll wall murals.

It does all this while staying rooted in its community. The Jupiter acts as an incubator to help get small businesses off the ground, and regularly hosts fundraising events and markets that highlight the work of local artisans.

The Jupiter’s love for its city is clear: this is a hotel that wants you to get out and play, and it knows all the best places. Your room key entitles you to discounts and extras at cool indie boutiques, neighborhood restaurants, and (of course) breweries, while there are special deals on tours from rafting trips to wine tasting.