In Edward the Confessor's time the land was part of the estate of Aluric, the King's thane and is only recorded in the Domesday Book as 'Chowdesbury', a part of the manor of Draiton valued at 100 shillings (£5).
Magno le Breton who held the manor under a tenancy to one Helgist would have valued the hilltop area for its summer pasture supported by reliable springs feeding ponds.
From the record of land use the area was still heavily wooded being able to sustain 200 hogs.

During this period Cholesbury still would have been a small, temporary settlement.
Over the next 150 years a permanent hamlet was established remaining part of the Drayton estates and a typical example of a Chiltern strip parish.
In 1091 the le Breton family although retaining ownership, passed control of the land and the income to the Knights Templar who when dissolved in 1312 passed it subsequently to the Knights Hospitaller as an endowment to the Commandery of Hogshaw.
After this period Cholesbury gradually detached from Drayton Beauchamp and became a separate manor, developing into a village community indicated by the construction, within the hillfort, of an early 12th-century church dedicated to St Laurence.
This is one of two churches, both incidentally called St Lawrence, to be found within hillforts in the Chilterns.
The other is at West Wycombe.

By the reign of Henry III around 1248 the population was large enough to warrant Cholesbury being split off as a separate manor, still controlled by the le Bretons.
The church was enlarged with the adding of a porch and its importance recognised with the appointment of a resident parson by the name of Abel.
Around 1330 Thomas Perot became Lord of the Manor of the estate where Parrott's Farm is today.
But independence was short-lived with its association with Drayton Beauchamp being re-established in 1336 when taken control of by Mary the Dowager Countess of Norfolk.
The family granted the estate to Edward II but in 1364 it was passed to Thomas Cheyne.
Full independence from then manor of Drayton Beauchamp finally came in 1541 when Robert Cheyne sold the manor to Chief Justice John Baldwin.

In 1618 John Baldwin sold the manor to one Thomas Stile, one of the attorneys of the Court of King's Bench.
By 1650 the rights attaching to the Lord of the Manor were transferred to the Seare family who also held the manor in neighbouring Hawridge.
Until the middle of the 18th century, Cholesbury continued to be just a chapelry under the administration of the parish of Drayton Beauchamp.
The establishment Cholesbury as a separate ecclesiastical parish was sanctioned by the Bishop of Lincoln in 1756.
In Edward the Confessor's time the land was part of the estate of Aluric, the King's thane and is only recorded in the Domesday Book as 'Chowdesbury', a part of the manor of Draiton valued at 100 shillings (£5). Magno le Breton who held the manor under a tenancy to one Helgist would have valued the hilltop area for its summer pasture supported by reliable springs feeding ponds. From the record of land use the area was still heavily wooded being able to sustain 200 hogs.
During this period Cholesbury still would have been a small, temporary settlement. Over the next 150 years a permanent hamlet was established remaining part of the Drayton estates and a typical example of a Chiltern strip parish. In 1091 the le Breton family although retaining ownership, passed control of the land and the income to the Knights Templar who when dissolved in 1312 passed it subsequently to the Knights Hospitaller as an endowment to the Commandery of Hogshaw. After this period Cholesbury gradually detached from Drayton Beauchamp and became a separate manor, developing into a village community indicated by the construction, within the hillfort, of an early 12th-century church dedicated to St Laurence. This is one of two churches, both incidentally called St Lawrence, to be found within hillforts in the Chilterns. The other is at West Wycombe.
By the reign of Henry III around 1248 the population was large enough to warrant Cholesbury being split off as a separate manor, still controlled by the le Bretons. The church was enlarged with the adding of a porch and its importance recognised with the appointment of a resident parson by the name of Abel. Around 1330 Thomas Perot became Lord of the Manor of the estate where Parrott's Farm is today. But independence was short-lived with its association with Drayton Beauchamp being re-established in 1336 when taken control of by Mary the Dowager Countess of Norfolk. The family granted the estate to Edward II but in 1364 it was passed to Thomas Cheyne. Full independence from then manor of Drayton Beauchamp finally came in 1541 when Robert Cheyne sold the manor to Chief Justice John Baldwin.
In 1618 John Baldwin sold the manor to one Thomas Stile, one of the attorneys of the Court of King's Bench. By 1650 the rights attaching to the Lord of the Manor were transferred to the Seare family who also held the manor in neighbouring Hawridge. Until the middle of the 18th century, Cholesbury continued to be just a chapelry under the administration of the parish of Drayton Beauchamp. The establishment Cholesbury as a separate ecclesiastical parish was sanctioned by the Bishop of Lincoln in 1756.
Cholesbury