Stay bold. Stay colorful. Staypineapple.Seattle - Portland - San Francisco - San Diego - Chicago


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 and Chicago. 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

University Inn

University District
Get Hip At University Inn Book Now
If you’re into Mid-Century mod, make this your home base. Just four blocks from the University of Washington, University Inn is known for 1960s-style groovy décor and award-winning organic cuisine. Hotel Details


Why would you go to one of America’s most unique, unconventional cities and stay somewhere standard? Hotel Rose is right in line with the city’s motto, “Keep Portland Weird.” It is nothing if not unique with bold, bright colors and style for days.

Hotel Rose

A Small But Mighty Portland Hotel Book Now
Bigger isn’t necessarily better. This gem may be a bit off-the-wall but it’s splashy style fits perfectly in this anything-but-dull town. Hotel Details

San Francisco

Glitz and glam on the edge of Union Square. What could be more fabulous? Elegant yet comfortable, this jewel box hotel offers ideal access to the best of San Francisco: The Golden Gate Bridge, Fisherman’s Wharf, Alcatraz and more.

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, Millenium 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