JOIN OUR SPOOK-TACULAR DOG COSTUME SHOWDOWN FOR A CHANCE TO WIN PAW-SOME PRIZES

Unleash your creativity and enter your dog into Dash, The Pineapple Pup’s Costume Contest!

Hospitality RedefinedBecca EdwinsOctober 10, 2024Halloween, Pineapple Pup Costume contest, Seattle, San Diego, San Francisco, Portland, New York City, Boston, Chicago

PUT YOUR PAWS UP FOR NATIONAL DOG DAY

Celebrate the special furr-iend who fills your life with happiness!

Hospitality RedefinedStaypineapple HotelsAugust 26, 2024International Dog Day, National Dog Day, Pineapple Pup, Hotel Dogs, Pineapple Pup Package, Seattle, Portland, San Diego, San Francisco, Chicago, Boston, New York City

WE’RE A WINNER OF USA TODAY 10BEST READERS’ CHOICE AWARDS

Staypineapple Chicago ranks #3 for the Best Boutique Hotel in the nation!

Hospitality RedefinedStaypineapple HotelsAugust 21, 2024Chicago, USA Today, Best Boutique Hotel, Readers' Choice

#WINNING: HERE’S TO ANOTHER YEAR OF SCOOPING UP TRIPADVISOR TRAVELERS’ CHOICE AWARDS

Staypineapple hotels have once again landed top spots on Tripadvisor!

Hospitality RedefinedStaypineapple HotelsJune 14, 2024Seattle, Portland, San Francisco, San Diego, Boston, Chicago, New York City

NOW OFFERING THE YAPPILY EVER AFTER DOG WEDDING PACKAGE

Give your four-legged friends the ceremony they’ll bark about for a lifetime!

Surprise and DelightStaypineapple HotelsApril 1, 2024April Fools, Seattle, Portland, San Francisco, San Diego, Chicago, New York City, Boston

CORE MEMORY: THANKSGIVING IN THE CITY

Austin and his partner had a festive holiday experience at Staypineapple Chicago, watching the Thanksgiving Parade before exploring the nearby Christkindlmarket.

CORE MemoriesStaypineapple HotelsMarch 21, 2024Chicago

Good Housekeeping Names Staypineapple as The Most Pet-Friendly Brand of 2024

2024 Most Pet-Friendly Hotel Brand

Hospitality RedefinedStaypineapple HotelsNovember 15, 2023Hotel Awards, Good Housekeeping, Seattle, Portland, San Francisco, San Diego, Chicago, Boston, New York City

WE HAVE A WINNER!

Thank you all for participating!

Surprise and DelightStaypineapple HotelsNovember 6, 2023Pineapple pup contest, Costume, Dog Costume, Contest, Hotel Contest, Pineapple Pup Costume contest, Pet friendly, Pet-Friendly, dog hotel, Pineapple pups, Seattle, Portland, San Francisco, San Diego, Chicago, Boston, New York City

Staypineapple + wear blue: run to remember

Help us support a great organization!

Surprise and DelightPeter HandOctober 31, 2023Seattle, Portland, San Francisco, San Diego, Chicago, Boston, New York City, Wear Blue, run to remember

HAPPY HOWL-O-WEEN!

Win a free 2-night stay

Surprise and DelightStaypineapple HotelsOctober 9, 2023Seattle, Portland, San Francisco, San Diego, Chicago, Boston, New York City, Pup Costume, Dog Costume, Free hotel stay, Hotel Contest, Halloween, Pineapple pups, Pet-Friendly, Pet friendly

CELEBRATE INTERNATIONAL DOG DAY

Share your Dash coloring page with us

Hospitality RedefinedStaypineapple HotelsAugust 26, 2023Pet-Friendly, Dog hotel, Dog-Friendly, International Dog Day, Seattle, Portland, San Francisco, San Diego, Chicago, Boston, New York City

SHOW US YOUR PINEAPPLES!

Enter for a chance to win a 3-night stay!

Staypineapple HotelsJune 19, 2023Seattle, Portland, San Francisco, San Diego, Chicago, Boston, New York City