Owner Stephen GrossAfter several years in mortgage banking and a career in historic preservation, Stephen Gross created the Clarendon Square, a Boston, Massachusetts bed & breakfast. Many years of travel to dozens of countries help him to be an expert host. His passion for guest satisfaction and interior design drive the Clarendon Square standard. What Stephen loves most about the bed and breakfast experience is sharing stories and meeting guests from all around the world. When time allows, Stephen travels to experience boutique hotel properties around the country.



GM Bobby Ciletti

A graduate of Boston University, Bobby Ciletti is the public relations and marketing manager for Clarendon Square. As a lifestyle and travel expert, Bobby is also the founding editor of The Days of the Chic a online destination for simply elegant living. After many years of lively discussion with guests at the Inn, & an extensive list of personal destinations, Bobby now shares his knowledge with the broader community. Feel free to peer into his world and a fun life that extends beyond Clarendon Square .


Innkeeper Jasmina Bakir


Gabriella Iarrobino - General Manager. Born, raised and having attended college in Boston, Gabriella is a true local. With a degree from Emerson College in Marketing & Communications Gabriella utilizes her skills in managing daily operations and in planning for future improvements. Her professional background is in customer service and advertising, bringing a valuable set of skills to the Clarendon Square team. After hosting guests each day, Gabriella entertains friends at home for dinner parties, enjoys attending concerts, and is attempting to try every restaurant in Boston.


Housekeeper Winnie Tan



Having emigrated from Canton China, and now a US citizen, Winnie Tan has lead the Clarendon Square clean team for almost 10 years. Her attention to detail is unparalleled. She has a mighty task, yet always finds a way to bring joy to everyone's day. Winnie lives nearby with her son and extended family members.