Staycationing is a surprisingly engaging hobby. Yes, you’ve heard of the Heathman Hotel, but did you know it’s a really cool destination unto itself? Or that there’s an adorable condo neighborhood along the river below the Kimpton RiverPlace? You’re probably more familiar with the hotels in other cities, like Seattle or San Francisco, because that’s how residing someplace works. Perhaps you occasionally visit the bars or restaurants of hotels minutes from your doorstep, but your rarely set foot in the rooms (affairs notwithstanding).

And so I considered a new pastime: sleeping around Portland. I booked rooms in five luxe hotels in or near downtown, all of which have been through the ringer in recent years: Early in the pandemic, the Jupiter Hotel served as a shelter, and both the Heathman and Kimpton Vintage changed ownership this year. All have trained their valets and front desk staff in how to engage with potential street crime, and they’re seasoned—indeed, as a guest, I did not have any negative experiences on that front. 

I know what you’re thinking. It’s difficult to justify a staycation. You could just stay in your bed at home. Which would be free. Why bother with the hassle of going somewhere? But a staycation in Portland buys you time. The short commute physically separates you from household projects (laundry baskets, those shelves you’ve meant to clean since 2022) and failure piles (those Amazon purchases you didn’t return, that stack of unread books). You can be reminded of the joys of your city, and might even focus on a romantic partner for more than 12 minutes. At the end: a quick jaunt home.

The Nines Hotel

525 SW Morrison St
This property’s crown jewel is Departure, the freshly renovated, 15th-floor, vaguely airplane-themed restaurant with jaw-dropping city views of historic Jackson Tower and surrounding skyscrapers. This is where you go to nosh on pan-Asian food, sip one too many Lucky Number Seven cocktails, and collapse into bed. If there’s a concert on at Pioneer Courthouse Square, wander over there, too—you can catch the 32nd Annual Tuba Christmas on December 16. (Yes, it’s a thing, and you should go). 

My one-bedroom suite was quiet, hip, and enormous, and felt more like the hallway to a room than a room. But in the sleek, masculine space with windows overlooking the interior six-story lobby atrium, I couldn’t relax. I kept thinking, “I like my bed. My bed is 12 minutes from here.” Before midnight, I made my way through the coquetry of valets, one of whom was restraining another from a sharp-tongued patron. By the time I got my car key, the restrainer was being held back from clocking the same patron, who finally got in his car and drove off. I double-tipped, and drove off, too. 

The metric for a good staycation, it turns out, is whether the allure of the hotel room surpasses the magnetic pull of one’s own bed. It’s a much higher bar than, say, a place to collapse into after a long flight. While the Nines would more than suffice on a business trip, it didn’t win out when a cozier option called. 

Kimpton Hotel Vintage Portland

422 SW Broadway
You might book a night at the Hotel Vintage for a staycation, but you linger for the lighting game: the lamps and light fixtures are thoroughly curated, from ’70s retro hanging pendants to lamps based with modern twisty wire. Every time I turned a corner I thought, “What masterpiece of lighting will I soon behold?” Upstairs are three rooms with balconies holding jetted tubs. Bring a bathing suit, unless you want to, as my mother would say, put on a show for the neighboring parking garage and hotel. It’s a truly lovely spot to watch the sky darken, the passing birds and, later, bats; the graffiti-covered fencing surrounding the hot tub is, apparently, a design choice from the hotel’s recent renovation. 

When your skin grows pruney, the second-floor game room is worth a stop for its barnwood shuffleboard table, magnetic wall Scrabble, giant Connect Four, billiards, and, this being Hotel Vintage, a hanging chandelier of green beer bottles. The flag-of-Italy colors on the awning of Il Solito restaurant made me think the hotel sported a pizzeria, but it is, in fact, a delicious and fast source of house-made pastas and must-order sausage soup with kale and carrots.  

I successfully stayed overnight and on to midday checkout, perched in the bed with my laptop, and the balcony door flung open to the aroma of the bakery across the street.

Jupiter Next

900 E Burnside St
This is not where you bring the kids: Jupiter Next’s do-not-disturb sign says “Tied Up,” and a showerer’s silhouette is visible to the room through frosted glass. The fridge holds 20 cans and bottles of alcohol, plus six more in the minibar (four Jamesons and two Underwood pinots), alongside CBD gummies. No Bible, though you’ll find The Four Truths: A Practical Guide to Personal Freedom. The narrowing of activities is further reinforced by the minimal extras: just you, a bed, and substances, with hip 20- and 30-somethings above in a bar called Hey Love. 

“Would I stay?” I wondered. I spent my minutes in the elevator trying to name the celebrity headshots on the walls and then marveled at the room’s stripped-down sleekness, furnished by an 18-foot piece of black wood built into the wall that does triple duty as a shelf, desk, and sink stand. There’s also an octagonal chair that looks like it was designed in CAD. 

I stayed. I watched a rerun of the Westminster Dog Show, in which a dog resembling a toupee with legs won second place. The six-story hotel is formidably soundproofed, and there’s a comfy bed and floor-to-ceiling windows that display a nighttime star show. For breakfast, head down a block to Grendel’s Coffee House, where the yogurt with compote is a treat. 

The many notices stating that the “Jupiter is not responsible for any damages or theft to vehicles or vehicle contents” indicates that drivers should opt for the $25 underground garage, which fills up—reserve in advance.

The Heathman Hotel

1001 SW Broadway
The Heathman is where stars performing at the Arlene Schnitzer Concert Hall usually stay, stealthily swept into the theater through a secret door that connects the buildings—and the hotel is plenty good enough for you, too. 

The hotel appeared in the novel 50 Shades of Grey and still attracts fans, but that’s not the vibe. Its showpiece is a soaring-ceilinged library with over 3,000 books accessed by ladders-on-wheels, where you can plop down on a couch and read. The 97-year-old hotel is on the National Register of Historic Places and has already survived a 1950s round of downtown blight, when retailers moved to the suburbs. In March, it was purchased by Aparium Hotel Group, a company that owns a dozen unique, often historic hotels nationwide. Guests are well dressed by Portland standards, and there’s a busy hum to the quite-good-but-not-exquisite restaurant, where the ratio of waitstaff and chefs to diners is the highest I’ve seen in town.

Snag a deluxe corner king room on a high floor, which will be decorated in blue, gray, and white, with midcentury-modern furniture that you’ll want to pack home with you. If you don’t want to engage with downtown, you don’t have to. Enjoy a lovely night of dining or theater or reading, followed by morning exercise in the sleek gym that includes the usual accoutrements, plus two Pelotons and an interactive Mirror screen. I would very happily stay for a week. It was my favorite of the bunch.

Kimpton RiverPlace

1510 S Harbor Way
The showstopper at the Kimpton RiverPlace is sunrise on the river, where the golden orb peeks over the eastern horizon and shines into your room. Birds frolic near the canoe dock while you order room service from the King Tide Fish & Shell restaurant. A close second is wandering southward outside along the waterfront loop at night, past bustling restaurants and bars, and peeking in the windows of fancy condos. It’s a scene. 

You want a King Studio Suite Willamette River View, which had my favorite layout: a living room with a fireplace, a luxurious bathroom with a tub that seconds as a hot tub, and a cozy bedroom. It is studiously trying to be comfortable, not cool. The rooms haven’t been updated in a while but are neat and snug in an earthy palette, reminiscent of late-’80s opulence and textured layering (the carpet, seating, wallpaper, drapes, center table, and fireplace each feature different patterns). 

The restaurant is a hit. Don’t miss the beet and watermelon salad, which is presented as a cake; the Japanese curry empanadas; and the seafood stew. While the restaurant has a view, you’ll want to wander around outside, where bikers and families and joggers streaming by along this lovely stretch of waterfront remind you of the true range of people in Portland.