The Maundbury Inn was established in the summer of 1929 by Thomas O'Reilly, a 3rd generation irish imigrant whose grandfather, Seamus O'Reilly, made a small fortune mining borox out in the mid-west, coming to Maundbury to settle in for a quiet life "by the sea."

The Inn was originally a mansion owned by Hamilton Armitage and had been a part of the Armitage Estate for generations. Hamilton died in 1822 bequeathing only his wealth to the town to be used for his library. During the auction of his possessions most were acquired by the Maundbury Historical Society though they lost the mansion to Seamus O'Reilly, who seemed quite adamant in purchasing the home.

Later that year Seamus moved into the mansion with his wife, Clara O'Reilly and their three children, Shane (Age 11), Ryan (Age 7) and Leah (Age 3) and lived there for approximately three months. Late one October evening the family vacated the home rather abruptly, leaving many of their belongings behind. They stayed at a dockside inn in Greyhaven Port until a house was built for them in Tattershall. It was often said when Seamus was pressed about why his family fled he would blanch and decline to speak on it any further. It was rumored the Maundbury Historical Society made many offers to Seamus for the mansion but he refused to sell.

Decades later his grandson Thomas (son of Shane O'Reilly) spent years attempting to renovate the mansion to modern living standards against some of the elder family members' wishes. The construction, however, was often plagued with mysterious accidents. Construction haulted shortly in 1928 when a contractor was found dead, having hung himself in a closet. After a lengthy investigation the police deemed it a suicide and the renovations were able to continue.

Thomas spent almost the entire share of his inheritance turning the mansion into an Inn. He named it after the town and it enjoyed several years of success though as tourism dwindled down the inn became more of a roadside attraction. The Maundbury Historical Society had it declared a historical landmark in 1953. It is still operated by Thomas O'Reilly's daughter Heather Broomsfell (nee O'Reilly).

Since its opening in 1929 several guests have complained about strange happenings that occur within the mansion. Most complaints include whispering between the walls late at night, furniture being rearranged or items mysteriously disappearing, most notably books which are often found open on the table in the common room the next day. When asked about these occurences Mrs. Broomsfell has been just as tight-lipped as her forebears.