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Stay comfortable. Staypineapple.Seattle - Portland - San Francisco - San Diego - Chicago - Boston


Urban Escapes Await

In a world of cookie cutter hotels, here’s a breath of fresh air: Staypineapple proudly offers fun, funky and fabulous accommodations to forward-thinking travelers in Seattle, Portland, San Francisco, San Diego, Chicago and Boston. Outfitted with colorful, stylish décor, each of our hotels offers it’s own one-of-a-kind ambiance.

When you Staypineapple, you’re staying in a hotel that fuels your desire for cosmopolitan adventure.


It’s home to so many iconic things—the Space Needle, Pike Place Market, Starbucks, Microsoft—that sometimes the equally amazing scenery gets overlooked. With all there is to see and do here, be sure to pack comfy shoes along with your sense of adventure!

Hotel FIVE

Far From Standard, Close To Everything Book Now
Hotel FIVE’s fun and funky décor fits right in with the vibrant city around it. There’s no better jumping off point for exploration. Hotel Details


The city’s motto is “Keep Portland Weird,” and for good reason. This hipster capital of the country is nothing if not unique thanks to its world-beating doughnuts, unnatural obsession with Elvis and even an annual naked bike ride (hey, it’s for charity).

San Francisco

If you’re an adventure-around-every-corner type of person, pack your bags. San Francisco offers endless exploration: The Golden Gate Bridge, Fisherman’s Wharf, Alcatraz and wine country are just the tips of the excitement iceberg. Ready, set, go.

The Alise San Francisco

Union Square
Charm in the Heart of San Francisco Book Now
Two parts glitz and glam, two parts elegant and comfortable—this jewel box hotel is a true gem. What’s more, it’s perfectly situated just minutes from famous Union Square, Moscone Center and endless shopping, dining and nightlife. Bring comfy walking shoes. Hotel Details

San Diego

Sun, surf, sand and sizzle—this city has it all. Year-round perfect weather and miles of pristine beaches make San Diego one of the best vacation spots anywhere. Be prepared to make some memories in the Gaslamp District, Balboa Park and Sea World.


If this isn’t the funnest (is that a word?) city ever, it’s darned close. Wrigley Field, The Loop, Michigan Avenue, Millennium Park and miles upon miles of world class dining, shopping, music, art and architecture. Just try to have a bad time.

The Alise Chicago

The Loop
Sleeping In a National Historic Landmark? That's Fun. Book Now
Back in the day this hotel was an office building—now all of the original office doors (complete with vintage knobs and mail slots) are the portals to our rooms. Here, the historic touches of a 19th Century building blend seamlessly with sleek, stylish, state-of-the-art amenities. Perfectly located in The Loop, The Alise Chicago is just steps from the city’s most iconic attractions. Hotel Details


Between its history, storied universities, and iconic sports teams, Boston is one of America’s premiere cities. It’s an easy city to walk with eclectic neighborhoods and cobblestone streets, so be sure to pack comfy shoes and multiple layers!