There are five single-gender dormitories on campus, all of which are home to several faculty members and their families. Additional faculty members live in campus housing scattered throughout the 104-acre campus. Although each dorm differs in design, all living quarters for students have a main lounge area with a television. The majority of rooms are designed for two students, though there are some single and triple rooms also available.

Attending a college preparatory school like Cheshire Academy is one of the best ways to prepare for life at college. Boarding school provides a safe environment for students to explore their independence and learn to take responsibility for their own lives. Living on campus provides students the structure and adult guidance they need to build self-reliance and maturity that will serve them well in college and beyond. Dorms at Cheshire Academy are more than just a place to sleep and study. These residential homes are also a place to unwind, study, talk to friends, listen to music, play games, and find time to be alone. Living together on campus helps students and faculty to bond and forge lifelong connections, and friendships built here continue long after graduation.