The Middlebury Inn is comprised of two floors and a total of 71 comfortable, elegant guestrooms. The main house features carefully restored guestrooms, some with sitting rooms, and all offering updated conveniences. The Porter House Mansion, adjacent to the main inn, is a stately brick mansion built in 1825. It houses nine guestrooms including a two-bedroom luxury suite and a wheelchair accessible guestroom, all styled in Victorian elements.
In the 1960s, two annex buildings were erected adding 20 more guestrooms in a more contemporary settings. Some of the rooms included in these buildings include extended-stay guestrooms equipped with kitchenettes, queen beds, and queen-sized sleeper sofa.