The Inn at Strawbery Banke or Holbrook House, as the building was known for over a century, was in existence before 1814. The great Portsmouth Fire of 1813 destroyed the entire center of town, as evidenced by the lack of wood frame buildings from Court Street to the river. The new ordinance forbade wooden construction in the area.

Samuel Holbrook, ropemaker and Robert Holbrook, sailmaker are listed on town records in 1821. By 1827, Robert Holbrook, Jr., also a sailmaker was in residence on Pitt Street (Court Street) as was his son John. The property remained in the Holbrook family until early in the 20th century from which time it has been a residence, rooming house and apartments.

In 1981, the Inn of Strawbery Banke was created using three upstairs rooms and with owners occupying the first floor. Over the next six years, the owners' apartment was created at the rear plus additions formed the breakfast room and an office with a room above. This gave a total of five rental rooms including one in the garret. Since Sally became innkeeper in 1990, two additional first floor rooms have been converted and private baths (showers) provided for all rooms. Now there are three first floor rooms and four on the second. All are tastefully decorated and comfortably furnished. Sitting rooms are on each floor with television and telephone.