Welcome to The Chester – A Hidden Gem in Boston’s Historic South End

Step back in time and experience Boston’s rich history in a modern setting at THE CHESTER, a boutique hotel nestled in the heart of the vibrant Chester Square neighborhood in the South End. Originally built in the mid-1800s, our charming brownstone has been thoughtfully restored to offer a perfect blend of historic elegance and contemporary comfort.

With just seven uniquely designed rooms, our intimate little hotel offers personalized service and an atmosphere that feels like home. Each room reflects the character of our historic property, while offering all the modern amenities discerning travelers expect.

A Neighborhood Steeped in History

Located on the corner of Massachusetts Avenue and Tremont Street, The Chester sits in one of Boston’s most dynamic and storied neighborhoods. The South End, once known for its Victorian brownstones and picturesque tree-lined streets, is now a vibrant community filled with art, culture, and a thriving restaurant scene. Chester Square itself, a historic landmark, has witnessed the evolution of this neighborhood from a 19th-century residential enclave to the bustling, culturally rich area it is today.

A Thriving Hub of Culture and Cuisine

The South End is celebrated for its diverse array of restaurants, cafés, and boutiques. Whether you’re in the mood for a cozy brunch, a farm-to-table dinner, or a quick coffee, you’ll find an endless variety of options just steps from our door. Explore art galleries, locally owned shops, and enjoy the lively street life that defines this eclectic neighborhood.

Your Gateway to Boston

Our prime location offers more than just the charm of the South End. You’re just a short walk from the iconic Back Bay, home to high-end shopping on Newbury Street, the stunning architecture of the Boston Public Library, and the beauty of the Charles River Esplanade. With convenient access to public transportation, including the nearby Orange and Green Line stations, all of Boston’s major attractions—from Fenway Park to the Freedom Trail—are within easy reach.

At The Chester, you’ll enjoy the best of both worlds: a peaceful retreat in a historic building, with the excitement of Boston right at your doorstep. Whether you’re here for business or pleasure, we invite you to discover the unique charm of our boutique hotel and the vibrant neighborhood we call home.

Experience Boston in style and comfort at The Chester—where history meets modern luxury.