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Relatively little is known about the De la Beres prior to their acquisition of Weobley Castle. Traditionally the first to live in England was one Richard De la Bere, a Norman or, more likely, a Breton, who came across with William the Conqueror in 1066 or soon after. However, he does not seem to have settled in the family's traditional home of Herefordshire and it is unclear where the family first held their lands.

It is possible that they initially settled in Kent or Sussex. In the late twelfth century Richard's great grandson John De la Bere married Joan, daughter and heiress of Stephen, Lord of Hever in Kent; and two generations later, in a law suit dated 1277, Simon De la Bere was described as of "Tornham" in Sussex. This latter place would appear to be Thornham, on the Hampshire border. No further connection has so far been found between this area and the De la Beres; but it is interesting to note that this same Simon De la Bere was the first person known to have used the De la Bere arms, which itself may have Sussex associations. It is described in the St. George’s Roll (1285) as Azure, a bend argent, two cottises and six martlets or. Martlets or swallows still appear on the coat of arms of the county of Sussex today. They are taken from the arms of the Lordly Norman family of Arundel, the earliest people to display the martlets which were also known as ‘hirondelles’. Several of their retainers are known to have adopted similar arms using these birds to show their allegiance. Perhaps the A’Bears were among them.

In 1279, Simon is known to have owned lands in Downton, in Wiltshire, which he conveyed to Roger Stepesham, but no further Wiltshire connections have been found. From the mid-thirteenth century onwards, the De la Beres had been marrying ladies of well established Welsh border families. They had certainly been Lords of the Manor of Stretford, near Leominster, since at least 1304, as illustrated by the beautiful old monuments in the parish church to Simon’s son, Richard, and his wife, Sybil (De Harley) (c.1320) and their son, also Richard, and his wife, Margaret (Gamage) (c.1340). Richard De la Bere Senior of Stretford also appears to have been the first to be associated with South Wales, acquiring lands in Knelston on the Gower Peninsula in the early fourteenth century. Hence his son, David De la Bere of Weobley Castle, obtained the job of steward to the local Lord [See the De la Beres of Weobley]. Possibly a second son was Thomas, one of the Chaplains at the Beauchamp Chantry Chapel of Stoke-sub-Hamden Castle (Som). The chapel had been set up by the second cousin of his sister-in-law, Margaret De Gamage.

The Close Rolls of 1297, however, give further clues to the movements of the De la Beres. Simon is here described as owing, with others, 60 marks (£40) in the County of Oxfordshire and it seems that the Thames Valley area may have also been one of their main stamping grounds at this time. In 1316, the latter Richard, was MP for Oxfordshire, and he is known to have collected the lay subsidy tax in Shiplake (just over the border from Wargrave) the following year. In 1318 he was appointed Sheriff of Berkshire, and was again MP for Oxfordshire in 1325. The family homes may have been the manor of De la Bere (or Bere Court), near Pangbourne, in Berkshire and the manor of Bear Place, near Wargrave.

The probable connections between John De la Bere (of Weobley Castle, d. 1389) and the village of Wargrave, in the early fourteenth century, have already been established [See The name A’BEAR]: but where in the parish did the family live? Bear Place in Harehatch, not far from Hill Farm appears to be the most likely candidate. It stands on the slopes of Linden Hill, once called Bear Hill. The site of the medieval manor house is clearly marked by the moat, which can still be seen today, not far from the present house. This was no doubt the place called "the Bere" mentioned in the inquisition post mortem of Sir John Harpeden, taken in 1438. An even earlier possible reference occurs in the Testa de Nevill (c. 1261) where it was reported to have been encroached upon by the Bishop of Winchester. No other records of early owners survive, but the Victoria County History of Berkshire records that this manor was always traditionally associated with the A'Bear family.