"The second Ace Hotel and the first step in the oh-so-cool brand’s expansion, the Ace Hotel Portland can arguably claim to have launched the current boutique hotel craze. Though it sounds like a cliché in this age of thoughtfully designed hotels, the contemporary icon—opened in 2007 in the 1912 building that long housed the Clyde Hotel—was one of the first hotels designed to feel like a cool, culturally savvy friend’s home. It’s decorated with works by acclaimed local artists, outfitted with vintage furnishings and handcrafted decor (including signature Pendleton blankets), and staffed by trendy hipsters who point guests to the hottest underground music shows. Hometown hero Stumptown Coffee Roasters opened one of its first cafés here, starting a partnership that has since taken the coffee halfway around the world to the Ace Hotel London . In Portland, the café simply helped define the Ace as the epitome of cool, a reputation that has only been further cemented by the opening of a popular farm-to-table restaurant and a subterranean cocktail bar. The true measure of the Ace’s cool factor, however, is that the hotel was parodied on an episode of Portlandia ."

"Situated on Northeast Portland’sAlbertaStreet, smack in the middle of the Alberta Arts District, Caravan is an unique alternative to the same old hotels or vacation rentals. The hotel is comprised of six tiny, individually styled houses for rent, from the cabin-like Skyline (made mostly from upcycled material) to the Amazing Mysterium (a vaguely steampunk affair modeled after a vardo gypsy wagon, with lovely additions such as stained-glass windows and lots of built-in shelving). In truePortlandstyle, the houses are clustered together in a “pod,” similar to how many of the city’s famous food carts are arranged. In lieu of a lobby, there’s a central outdoor common area with a fire pit (s’more-making is encouraged, and supplies are provided). Note that live bands perform for guests and a limited number of community members on Wednesday evenings during the summer months, and the whole area gets busy on the first Thursday of every month, when Alberta Street transforms into a pedestrian-only night market-cum-street party that lasts well into the evening."

"Don’t let Portland ’s low-key, outdoorsy-hipster vibe fool you: the Heathman Hotel is as grown-up and refined as they come. Opened in 1927 as an expansion of one of the city’s grande dame hotels, the Heathman continues to set the standard for classic luxury in the City of Roses. Rather than rest on its laurels, though, the hotel has consistently upped the ante, collecting a museum-worthy array of modern art (including a handful of Warhols alongside works by acclaimed local artists), boasting one of the most impressive collections of autographed books in the world, and offering guests a choice of mattress in the sumptuous rooms. Indeed, so famously decadent and romantic is the Heathman, with its award-winning restaurant and almost-nightly live jazz in the bar, that it was used as the setting for several of the rendezvous in E.L. James’ infamous Fifty Shades of Grey —although, for most guests, the original crystal chandeliers and marble fireplaces inspire magic enough."

"Rising from the ashes of the 60’s Red Lion Hotel is the east side’s latest entry into Portland’s hip hotel scene—the Eastlund. Cut from the same pedigree as the downtown Modera Hotel, the Eastlund is a welcome upgrade in the evolving convention center area. The fun starts in the bright, expansive lobby, where eye-catching art welcomes visitors. The staff is tuned to deliver exceptional customer service, and the vibe is genuine and unpretentious. Amenities include great food, local spirits, tech-savvy rooms, and super-fast Wi-Fi throughout the property. The rooms and public spaces put art front and center, while the meeting areas are wired for productivity. Business and leisure travelers also benefit from attention to detail and a staff committed to getting it if it’s not already available. The efficient, comfort-forward rooms boast big flat-screens and colorful décor, and the river and city views from the upper levels are spectacular day and night. An easy MAX ride from the airport, The Eastlund is also delightfully located within walking distance of a variety of transportation, entertainment, meeting, and dining opportunities. With so many on-site amenities, however, you might just find yourself pleasantly planted during your Portland stay."

"For a deal on a great room in an ideal location, you can’t do better than Hotel Rose. Following a major renovation, the property now features an understatedly hip vibe, wrapped in clean lines and comfort. The nice-sized rooms are bright, even on the dreariest Portland days, and come with all the trappings for spending lazy mornings in bed. There’s no shortage of wonderful things to do, eat, and drink as close as the lobby bar, but don’t stop there. Take a run or walk on the waterfront across the street. Wander uptown to Pioneer Square, take the MAX to the zoo, or grab a streetcar and head to the Pearl for some shopping. Hotel Rose makes it all simple, with a well-rehearsed staff keeping your stay as weird as you can tolerate. You are, after all, in Portland."

"Sure, the Hotel Vintage is classic (it was built in 1894 as the Hotel Imperial, one of Portland ’s most iconic grande dames , and is listed on the National Register of Historic Places), but its name references another kind of vintage: the many renowned wines of the surrounding Willamette Valley. When the hotel reopened in 2015 after an extensive renovation, it announced partnerships with 117 local wineries (one for each guestroom), each of which sends a representative at least once a quarter to pour at the guest-only wine hour held every evening. Rooms feature original artwork made from recycled corks, and the trendy lobby bar (named for Bacchus, the god of wine) and local landmark of a restaurant offer an impressive list of some of the best local and Italian wines. Even those who don’t share the hotel’s passion for vino will find plenty to love, from the famously superlative Kimpton service to the private outdoor hot tubs and custom Public bicycles available to borrow. Also on-site is a game room—an extension of the lobby bar where guests and in-the-know locals mingle over retro video game consoles (Atari, anyone?), shuffleboard, and pool. We’ll raise a glass to that."

"When you visit a too-cool-for-school city like Portland —you know, one full of hipster artists and musicians who spend their days sipping artisan espresso, brewing craft beer, and going for long bike rides through postcard-worthy terrain—the important thing is to determine where everyone hangs out. Well, stay at the Jupiter Hotel, and you’ll find you’re already there. In 1994, two local creatives took over a classic 1960s motor lodge in the East Burnside neighborhood (that is, just across the river from downtown) and transformed it into a hipster-chic boutique hotel and one of the city’s hottest nightlife venues, with a local brews- and spirits-focused bar and an intimate concert venue with live shows seven nights a week. Rooms are decorated with original murals by local artists, and the lobby doubles as a (very popular) art gallery. Thanks to the old motel layout, all rooms are oriented around two courtyards, and guests often leave their doors open for ventilation. Which is just to say that it should come as no surprise that, not only is the scene at Jupiter a lively one, but parties are welcome, and the atmosphere is festive until the wee hours of the morning. In other words: yes, this is where all the cool kids are."

"Housed in a converted elementary school dating back to 1915, this sprawling hotel complex has long drawn out-of-towners and local Portlanders alike with its bars, restaurants, miniature movie theater, and even a heated soaking pool that’s open to the public for a small fee. While these amenities—along with the hotel’s sprawling school grounds and proximity to the popularAlbertaArts District—are enough to make it one of the most attractive spots to stay in town, its real cred shines through in the 57 guest rooms, many of which are actually converted classrooms (and still have some of the original scholastic features, such as chalkboards, integrated into the room design). Don't leave without sampling some of the McMenamins signature brews in the Boiler Room Bar, housed in what was once the school’s boiler room."

"The Hoxton, Portland—the brand’s second outpost in the United States, after Brooklyn—sits in Old Town Chinatown, in a 1907 building that overlooks the statuesque Chinatown Gateway. With this property, The Hoxton arrives in the Ace’s hometown, successfully improving on the tried-and-true hostel model with small but well-priced rooms, a buzzy lobby with plenty of work space and strong coffee, and restaurants and bars that even locals love. The 119 rooms are divided into categories, starting with Shoebox and increasing in square footage to Snug, Cozy, and Roomy. The largest options have a small living area with two chairs and a table, and what the others lack in space they make up for in smart design (including closets that hold coffee kettles and safes). Additionally, guests can look forward to small touches like a complimentary “little breakfast” delivered each morning upon request; thoughtful maps with neighborhood highlights; and minibars stocked with essentials like water and milk for no extra charge. When you’re in the mood for something more substantial, there are three food and beverage spots, all run by chef Joshua McFadden's Submarine Hospitality group (Ava Gene’s, Tusk). Head to the ground-floor La Neta for seasonal, Mexican-inspired fare; the rooftop Tope for fantastic tacos and a long list of mezcals; or the nameless basement bar (look for the door marked “knock knock knock” on SW 5th Avenue), which offers classic cocktails in a dark, intimate space."

"Portland isn’t exactly the kind of city that’s known for being “fancy,” which was why it was so bold for the Starwood Luxury Collection to add a sleek 15th floor to the top of the iconic Meier & Frank department store building downtown—and turn the top nine floors into the swankiest hotel in town. Who would’ve thought that Louis XVI chairs, tufted white leather and teal velvet, crystal chandeliers, and ornate wallpaper would work so well in the city of plaid, beards, and twee bird patterns? In true Field of Dreams fashion, Starwood built it and the travelers came out of the woodwork, hungry for a luxury hotel that embodies the Rose City with everything from environmentally conscious practices and farm-to-table restaurants to an extensive art collection and rooftop honey bee colony. All that’s to say nothing of the private club-like Library, a collaboration with Portland icon Powell’s Books (the world’s largest bookstore) that allows hotel guests to borrow from a curated collection of 3,000 books during their stay. As it turns out, it’s not all that hard to dress Portland to the nines."

"The Portland-based Provenance Hotels group continues its domination of downtown with Woodlark, its sixth hotel in a six-block radius. With everything from an inviting lobby cafe and much-lauded restaurant to a modern design palette and a few smart nods to the property’s historic past, the hotel aims to be as appealing to locals as it is to visitors. Upon arrival, guests check in at a marbled horseshoe bar, staffed by baristas serving beans from local roaster Good Coffee. Also in the lobby is the Colibri flower stand from Naomi Pomeroy, a former Top Chef Masters star who also dabbles in floral arrangements. The hotel itself spans two buildings: the former Woodlark Building, which is on the National Register of Historic Places, and the Cornelius Hotel. No matter which you end up in, however, you can expect spacious rooms, with tall ceilings and large windows. Decor ranges from black-and-white plant images by Pacific Northwest photographer Imogen Cunningham to cozy details like plush headboards and dark wood accents and, while there aren’t any closets, there are racks with hangers and space for luggage. There are also mini bars with local goods like Underwood canned wine and Woodblock chocolate, plus USB ports built into the bedside tables for easy charging. Additional amenities include pet-friendly rooms with beds, bowls, and treats; a top-of-the-line gym with a Peloton bike and interactive workout wall; and Shinola bikes for cruising the city. When hunger strikes, head to Bullard (the Texas-meets-Oregon restaurant from Top Chef alum Doug Adams) or Abigail Hall (a bar in the Cornelius’ former library, which used to serve as a gathering space for women suffragists)."