The paintings belonging to Cheltenham Art Gallery & Museum form a rich and diverse collection that is rooted in the town's history and the wider Gloucestershire context. The most important collection is of Dutch 17th century paintings presented to the town by the 3rd Baron de Ferrieres, former Mayor of Cheltenham and MP, in 1898, including work by Jan Steen, Gabriel Metsu, and 'Self Portrait' by Gerrit Dou.
Highlights from the 18th century are the panoramic paintings of Gloucestershire and two works by Guardi both from Gloucestershire families. Cheltenham's nationally important Arts and Crafts Movement collection is reflected in work by artists linked to it including Sir William Rothenstein and Charles and Margaret Gere. There is also later 20th century and contemporary work reflecting the lively art scene in the county and including the work of nationally important artists with much given by the Contemporary Art Society. A highlight is 'Village Life' by Stanley Spencer painted during his stay at Leonard Stanley in Gloucestershire in 1939–1940.