A "Wicked Smaht" Choice in South End

Staypineapple Boston is the perfect launching point for your Boston experience whether you’re taking a walk along the Freedom Trail, in town on business, or looking to catch a game with one of Boston’s storied teams. Our location is in one of Boston’s finest neighborhoods, the South End, just steps away from Back Bay and many of the city’s famous historical sites, stylish stores, and great restaurants. Staypineapple Boston will help you relax while working on your accent in private with all the elements and comfort of The Naked Experience and Staypineapple amenities, giving you a modern hotel experience in one of our country’s most historic cities.