Be Spontaneous in Portland

In case you couldn’t tell from the name, this 782-room complex is all business: it sits just a block from public transportation on the MAX, and offers a ballroom along with 16,000 square feet of event space, plus two restaurants (a gastro pub and northern Italian grill) and complimentary access to two fitness centers and two indoor pools. Sleeping quarters are inoffensive and modern—in the Executive tower (the hotel is split between two buildings), rooms and suites benefit from more space and upscale amenities like minifridges, Keurig coffeemakers and L-shaped desks.

Property-wide free Wi-Fi, nightly wine hours and “companion” goldfish bowls (to relieve loneliness—yes, really)  have endeared Kimpton to the hearts of many a traveler, but this iconic property, opened in 2007, hits a special note. It’s housed in a National Register of Historic Places-listed former 1912 department store, and the quirky rooms reflect that history with richly upholstered furnishings, framed mirrors and vintage-inspired wallpaper (in addition, of course, to Frette linens, 32-inch flat-screens and minibars). Organic coffee is poured each morning in the lobby, and the contemporary American eatery—known for its extensive whiskey library—offers 24-hour room service.

Unlike its colorful sister property downtown, this Kimpton hotel channels rural Oregon with its front-row river views, abundant outdoor spaces and chalet-style lobby with a stone fireplace. Earthy, den-like rooms come with all the trimmings, while some suites even feature wood-burning fireplaces and kitchens; for longer stays, there’s a separate annex with condo units overlooking the marina. At Three Degrees, the hotel’s laid-back seafood grill, pull up a rocking chair on the heated, year-round porch, or settle inside for fresh oysters and Alaskan scallop crudo.

No, you’re not coming here for the Michelin-starred dining or the decor, but you could do worse than holing up at this cookie-cutter chain for a few nights. Set back from the Columbia River, it offers free shuttle service to the airport, which sits just 2.5 miles away, any time of the day or night. The rate also gets you free Wi-Fi, hot breakfast and access to the on-site gym and indoor pool. Need to heat up a can of SpaghettiOs for a quick pre-flight dinner? In-room microwaves and coffeemakers make eating on the fly a cinch.

Hostels are rarely short on personality, and this cozy, three-story Portland manse is no exception. The structure dates back to 1889—complete with a deck and a furnished patio—yet thanks to owner Jim Kennett’s intuitive touch, the rooms (both dorm-style and private) feel airy and bright, rather than antiquated. In line with its free-spirited clientele, the front desk remains open 24 hours, and there are bike rentals, free Wi-Fi and frequent organized activities like group dinners and pub crawls to keep travelers engaged. 

Making a last-minute pit stop on your road trip? Friend’s couch didn’t work out? Best Western is always a safe bet. With a grand lobby hall and a U-shaped layout that encloses an outdoor pool, hot tub and sundeck (perfect for catching a few rays, when the weather permits), the property is more resort-ish than you might otherwise expect—free cooked breakfasts are also a nice perk. Rooms are fully modern; we recommend requesting a private terrace or balcony overlooking the pool courtyard, otherwise you might end up facing I-205 across the street.

Within the Intercontinental Hotel Group (of which Staybridge Suites is a part), there’s a chain to suit practically every taste. This one’s for budget travelers who like built-in comforts while they’re on the road. If you have pressing work, there’s free Wi-Fi in all rooms, plus a cushy business center; if you’re catching a flight, a free airport shuttle runs 21 hours a day; if you’ve just come back from the Portland Farmers Market, there’s a full kitchen with a stove, cookware and a dishwasher in every room. Not to mention the 24-hour gym and heated indoor pool. Who needs Four Seasons, anyway?

If the idea of sleeping above a Macy’s seems tacky to you, consider that in 1909, when this 15-story building went up, department stores were upper-tier barometers of culture, offering exclusive glimpses into the latest designs, fashions and technology. In 2008, an $18 million renovation converted the top floors of this glazed terra cotta landmark into a luxury hotel, with a world-class contemporary art collection and regal rooms. But it’s the public spaces where this place really shines—take the light-filled atrium, which spans four floors and includes a library whiskey bar with a pool table and leather sofas. Departure, one of the hotel’s two eateries, serves upscale sushi on two rooftop patios overlooking the Willamette River.

In today’s celebrity-obsessed culture, a little old-school glamor goes a long way. Hotel deLuxe models itself after 1930s-era Hollywood—the vintage photographs of pouting starlets that decorate its plush lobby appear throughout the entire hotel, and there’s even a discreet cocktail bar called the Driftwood Room with a single curved bar and noir vibe that could be straight out of a David Lynch movie. Playing up the diva appeal, guests can indulge their wildest rooms service needs with a “Make It So” button on each telephone, and there’s even a Marlene Dietrich suite with an eight-foot circular bed.

As the hospitality trend moves toward ever tinier and more bespoke spaces, a classic mid-range tower like the Paramount can be refreshing. The down-to-earth property does just what it says on the box: warm interiors, spacious bathrooms with Gilchrist & Soames toiletries, and high-tech touches like free Wi-Fi, 37-inch HDTVs and MP3 clock radios—there’s even a tier of rooms and suites with chic French doors opening onto balconies with wrought-iron furniture. And for meals, there’s Swank, a bistro with rustic wood interiors, and a modern whiskey bar called Swine showcasing local spirits.