Find Your Piece of the PineappleSeattle - Portland - San Francisco - San Diego - Chicago

Unrivaled Boutique Accommodations

Urban Escapes Within Easy Reach

Creating memorable experiences for our guests is not just our specialty, it’s part of our legacy.

Staypineapple is proud to offer boutique accommodations to suit the needs of savvy travelers in Seattle, Portland, San Diego, San Francisco, and Chicago. Outfitted with stylish décor, each of our hotels is uniquely poised to offer a chic, inviting ambiance you’re unlikely to find elsewhere.

Discover a Staypineapple boutique hotel that meets your needs and fuels your desire for cosmopolitan adventure.


Home to the iconic Space Needle—and surrounded by lush forests and alluring scenery of mountains and water—Seattle is a staple landmark in the Pacific Northwest region with endless activities to keep you on your toes. Trust us, the rain won’t stop you.

Hotel FIVE

Quirky Downtown Seattle Hotel Book Now
Hotel FIVE invites guests to a true Seattle experience with its prime location to the city's top tourist attractions and eccentric decor. Hotel Details


Otherwise known as the City of Roses, Portland’s charm comes from its unconventional and unique city culture that thrives in the food, music, and art scene. And just a few miles out, you’ll find yourself surrounded by evergreen forests and enchanting waterfalls. Just don’t forget to “Keep Portland Weird.”

Hotel Rose

Portland Boutique Hotel Book Now
Get an authentic experience in the city of Portland with Hotel Rose, an off-the-wall boutique hotel in close proximity to all things that "Keep Portland Weird." Hotel Details

San Francisco

Don’t let the San Francisco fog scare you away. Known for the Golden Gate Bridge and high-tech startups, this metropolitan city is unmatched in its exciting activities. From Fisherman’s Wharf to the evening skyline, San Francisco is a city that will continually impress you.

San Diego

Sit back and relax in Southern California’s urban paradise, San Diego. The city’s incredible year-round weather and picture-perfect beaches make San Diego an irresistible vacation spot for anyone and everyone. Create unforgettable memories in the Gaslamp District or Balboa Park—you won’t be disappointed.


Home to the Loop, Wrigley Field and Logan Square, Chicago is a diverse destination for lovers of music, art, architecture and the good life. Full of charming features around every turn, exploring the city promises access to world-class museums, magnificent public parks, and chic, one-of-a-kind places to eat, drink and celebrate.

The Alise Chicago

The Loop
A New Chicago Boutique Hotel Book Now
Situated in the excitement of the Loop, The Alise Chicago combines impeccable style with access to the city’s best attractions, from theater to dining to fine art. Hotel Details