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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 New York, Chicago, San Francisco, Boston, Seattle, Portland, San Diego and growing. Outfitted with colorful, stylish décor, each of our hotels offers its own one-of-a-kind ambiance.

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

New York City

You know what they say: “If you can make it here, you can make it anywhere.” The city that never sleeps is home to Times Square, Broadway, Wall Street, championship sports teams, and just waiting to create its next star. Is that you?

An Artful Hotel

Midtown

Perfectly placed in The Big (Pine)Apple Book Now

With vibrant colors and the perfect touch of class, this centrally located boutique hotel in Midtown Manhattan is steps from Times Square, Madison Square Garden, Hudson Yards, and the Theater District. It’s the perfect jumping off point for any adventure that awaits you in the city so nice they named it twice. Hotel Details

Chicago

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.

An Iconic Hotel

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, Staypineapple Chicago is just steps from the city’s most iconic attractions. Hotel Details

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.

An Elegant Hotel

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

Boston

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!

A Delightful Hotel

South End

Anything But Boston Common Book Now

Thoughtfully located in Boston’s historic South End neighborhood, Staypineapple Boston offers a fun, comfortable stay in the middle of one of America’s oldest cities. Hotel Details

Seattle

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!

The Maxwell Hotel

Seattle Center

Stay in Style Book Now

Just steps from the Space Needle and other top attractions, The Maxwell Hotel offers a colorful interior and all the modern conveniences. Hotel Details

Hotel FIVE

Downtown

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

Watertown Hotel

University District

Get Urban in the U District Book Now

If open concept industrial is your speed, park yourself here. Concrete and wood accents anchor Watertown Hotel’s modern décor and it’s all just steps from the University of Washington campus. 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 steps from the University of Washington, University Inn is known for 1960s-style groovy décor. Hotel Details

Portland

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).

Hotel Rose

Downtown

It’s Always Sunny at Hotel Rose Book Now

This colorful character may be a bit off-the-wall but it’s splashy style fits perfectly in an anything-but-dull town. 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.

Hotel Z

Gaslamp Quarter

Gaslamp Quarter Getaway Book Now

Hotel Z is perfectly located in the historic Gaslamp Quarter, San Diego’s epicenter for dining, shopping and entertainment. Get ready to have some fun. Hotel Details