Charleston boasted several downtown hotels from around the turn of the 20th century. The northwest corner of the Kanawha Street (now the Boulevard) and Hall Street was home to the Hale House. It was torn down and in 1885, A.L. and Meredith Ruffner, along with the Charleston Hotel Company, built the stately Ruffner Hotel. The Ruffner Hotel was the 2nd largest building in the city after the Victorian Capitol, also built in 1885.

The Renaissance Revival style hotel had eight floors and basement with two elevators. The original building had a spire on the corner and an elegant portico facing the Kanawha River. The hotel had its own ferry to carry passenger from the hotel to the C&O railroad station across the river. After the completion of the South Side Bridge, vehiclular traffic was deposited practically at the hotels front entrance. Ruffner Hotel match books advertised the hotel as the ‘Commercial Man’s Hotel’ with rooms from $2 a night. It remained a quality hotel until its’ demise when the Ruffner was torn down in 1970.

The Kanawha Hotel was built at the corner of Summers and Virginia streets. Although initially eight stories high, the hotel was a rather narrow building. Later a fire-proof addition was built nearing tripling the size of the hotel. After the 1960 presidential primary, John F. Kenneday held his victory celebration at the hotel. The hotel later became home to the Charleston Job Corp. The Kanawha Hotel building was torn down in 2003.

The Holley Hotel was built in 1914 at 1008 Quarrier Street where a grocery store once stood. The quite large structure was a busy city center hotel for years. As more modern hotels were constructed in Charleston, the Holly, lacking modernization, lost the business clientele it once enjoyed. In 1966, hotel owner Frank Veltri began the tradition of serving a free Thanksgiving meal to feed anyone in need. The tradition continued there until the Holley Hotel was imploded on January 17, 1993.