Donnington is best known for its castle and the village has witnessed many fascinating events connected with it. From early times, the Abberbury family owned the manor and it was to Sir Richard Abberbury the Elder that King Richard II first granted a license to crenellate his house there in 1386. This included the building of the present gatehouse. Abberbury had been one of the young King’s guardians in his youth and later became Chamberlain to his wife, Queen Anne. Donnington has no parish church in the village. It stands at Shaw, but the parish is known as Shaw-cum-Donnington. There was once an old chapel at Donnington but, rather than rebuild it, Abberbury gave it to the Friars of St. Cross who founded a Friary there around 1376. It served the local community until its dissolution in 1538. Abberbury was also lord of the manor of Iffley in Oxfordshire which, in 1393, was given to support the founding of the Donnington Hospital, a charity providing almshouses for twelve poor men. It is the oldest charity in Berkshire and the 23rd oldest in the country!

Donnington Castle was later bought by Thomas Chaucer, son of the poet. He was also Constable of Wallingford Castle, and his main residence was at Ewelme in Oxfordshire; so Donnington probably saw little of its new lord. He did, however, take an interest in the almshouses and built his own, at Ewelme, on the Donnington model. By Tudor times, the castle had fallen into Royal hands and members of the Royal family sometimes visited. Their retainers no doubt filled all available accommodation in the village as well as the castle. On one occasion temporary dwellings had to be erected for them. King Henry VIII came in 1539 and 1541. Perhaps he wanted to scotch the rumours perpetuated by a Donnington Almsman that he was dead. The poor man was pilloried in Newbury and subsequently had his ears cut off! Princess Elizabeth was granted the castle by her brother but her sister, when Queen, would not let her live there. The villagers were kept fully employed when the building was completely refurbished for her eventual visit, as Queen Elizabeth I, in 1568. She later granted the stewardship to Lady Hoby of Bisham Abbey but gave the castle away to the Earl of Nottingham. The Earl let the new King James house his retinue there whilst on a trip to Shaw House. Lady Hoby was incensed and took a band of armed clothiers up to the castle from Newbury . The people of Donnington must have been terrified as the angry mob marched through the village before being repulsed at the fortress gates.

In 1602, the Earl of Nottingham refounded the old almshouses which he discovered in a state of disrepair. The present building on the main road dates from this time, although they were considerably restored after abandonment during the Civil War. By this time the castle was owned by the Parliamentarian Packer family, but, at the commencement of hostilities, it was quickly taken for the King and held by Sir John Boys. It was besieged for most of the war and its  guns held off the parliamentary army during the Second Battle of Newbury. The village was deliberately destroyed by Boys to stop the Roundheads finding shelter there and, after the war, there was much rebuilding to do. A ghostly re-enactment of a skirmish between a Royalist cavalry patrol from the castle and a superior parliamentary force from the town is sometimes said to still be seen in Love Lane.

The Packers lived mostly at Shellingford Manor in the north of the county, but, with the destruction of the castle, their residence when visiting Donnington became the old steward's lodge, now Donnington Castle House. In 1699, Robert Packer married Mary Winchcombe, the eventual heiress of her ancient family whose estates were centred on Bucklebury House. Thus the two manors became united, but while the lord of the manor transferred himself eastward, other great houses began to emerge in Donnington. The 'Priory,' originally converted from the old Friary but rebuilt after the Civil War, was the home of the Cowslade family, including the usher to Queen Charlotte. Donnington Grove was built for the historian, James Pettit Andrews in 1763, in Strawberry Hill Gothic style. He was half-brother of the lord of Shaw Manor. Twenty years later it was sold to William Brummell, the father of the King's great friend, Beau. Around this time, the Packer heiress and her husband, David Hartley, the famous physician and philosopher,  lived at Donnington Castle House for a whole year and considered making it their permanent residence, but in the end decided they preferred Bath and London.