By 1900, Battell’s enterprise exceeded the capacity of the Inn, and cottages were added to accommodate more guests. Special friends who summered regularly at Bread Loaf purchased lots with water and sewage rights, and with Battell’s assistance, built their own family cottages. The first two, Bridgman and Cornwall, were constructed across the street from the Inn around 1881, just south of a barn that Battell would raze in 1884 to improve his view of the sunsets. The stately Clinton Smith barn behind the Inn was built to replace it, housing his dairy, meat and Morgan horse breeding operations.
Cherry, Birch and Maple were the next three cottages added along the road, around 1902. Birch and Maple, both three stories tall with full wrap-around porches, offered private suites and baths. Completing the list of cottages built during Battell’s life are Hubbard Cottage (now Fritz), Hubbard Study (now the Printers’ Cabin), Treman and Gilmore. Battell painted the structures he built with the distinctive ochre color; buildings painted white were built after his death in 1915.
Ownership of the cottages has passed from the families to Middlebury College and today are reserved as accommodations for summer faculty, administrators, students and staff.