The Littledean House Hotel is a prominent building at the northern end of Broad Street. It was built in 1740 and was originally intended to be a coaching inn. It was used as a private residence of wealthy landowners and was converted to a guest house that first opened in 1903. In 1906 the boarding house became the Littledean Guest House. In the 1920’s and 1930’s the 80 roomed guest-house specialised in vegetarian meals.
In a 1951 brochure the Littledean Guest House had grounds extending to 12 acres with ‘spacious lawns amid beautiful scenery at 600 feet altitude.’ Guest could enjoy ‘our own milk and dairy produce’. Attractions included two hard tennis courts, riding, bowls, putting, billiards and snooker, table tennis, dancing and a library. ‘An ideal centre for the Royal Forest of Dean and Lower Reaches of the River Severn and the Lovely Wye Valley.’
Santokh Singh, who had previously owned the Mount Pleasant and the Swan in Cinderford, bought the Littledean House Hotel in 2004. He also owned the Oaklands Club in Cinderford. In an advertisement in the ‘Forester’ newspaper in September 2015 he said, “My recipe for running a successful pub is very simple. You serve good beer, good food and make people feel welcome when they come in.” In 2010 Santokh Singh leased the Littledean House Hotel to Richard and Kate Bond.
The Littledean House Hotel hosted the first Littledean Beer Festival in April 2011, the weekend of the Royal Wedding.