When W. H. Bowles wrote his "Records of the Bowles Family", published in 1918, he did not have access to the Internet and online searchable catalogues of historic documents preserved in archives spread across England.  Nor had the Church of England yet made its files available to public inquiry. 

Bowles believed that a branch of the Lincolnshire family had arrived in Kent in the 15th century:

"That there was a family of our name settled in Kent from very early times, and possessed of estates in the neighbourhood of Canterbury, is shown by numerous references in county records. The earliest known settlement of this family was in Shalmesford Street, a hamlet in the parish of Chartham, about three miles from Canterbury. The family house is described in the ancient charters as “Bolles Hall, a Mansion,” which gave its name to a manor of which the Bolles’ were lords. They also had possessions at Chilham and the adjoining parishes, in the city of Canterbury, and at Feversham, and elsewhere in Kent."

The existence of Bolles Hall is further supported by Edward Hasted who wrote in his 1798 "The History and Topographical Survey of the County of Kent", volume 7:

"THE MANOR OF SHALMSFORD-STREET, and afterwards, from its possessors, the mansion of Bolles, a family who had large possessions at Chilham and the adjoining parishes. At length, after they were become extinct here, which was not till about the beginning of the reign of Queen Elizabeth, this manor came into the name of Cracknal   further reference

The fact that the Bolles of Chartham re-named "their family house" (Chartham Manor) to be Bolles Hall was an indication to W. H. Bowles that this early line was connected to the ancient line of The Bolles of Swineshead and their Bolle Hall in Lincolnshire. This idea was further reinforced by their obvious wealth.  However, it now appears that the Boles of Chartham were a local Kentish branch, although possibly with Norman roots, who built up their wealth over a period of time through land ownership and the tanning trade.

The earliest sign of a Bole connection to Chartham is a grant signed between 1329 and 1350 involving Richard de Boles' land in Ickham (which had been in the Boles family since the early 1200's at least) which was apparently signed in Chartham as it was witnessed by Thomas Munde, Robert Torold and James upe Doune all of Chartham.

The next Bole reference I have for Chartham is an Exchange Agreement signed at Chartham in 1407 witnessed by William Bolle, John Petite and three others.  ref.  This is another pretty good indication of a connection between the Bolles of Canterbury and The Boles of Ickham as we know from a land grant from 1467 that the heirs of John Petyt of Shalmsford inherited land adjacent to the Boles land in Ickham.  Shalmsford is the village just SW of Chartham where William Bolle settled and is the location of the Bolles Hall.  However, in 1407 the Bolles not not occupied the Hall yet.  See The Boles of Ickham for more about the two other grants mentioned above. 

In 1412 Thomas Bolle jr. of Chartham leased 8 and 1/2 acres of land in Chartham from the Canterbury Cathedral Priory.  ref. 

The Will of John Darelle dated October 14, 1438 includes this: "I leave to the executors of the Will of William Bolle of Chartham 10 marcs."  ref. 

A grant to John Malvyll dated 1437 refers to his land "in Chartham parish with the King's Highway to south and the garden of Thomas Bolle to east"  ref.  and a lease dated 1462 refers to land in Chartham lying with "the land late of Thomas Bolle to the south, 'Malefeld' to west and the land of John Hewhet to north."  ref.  Note: from these two we can see that 'Malefeld' would be John Malvyll's field and that Thomas Bolle had just passed away in 1462 as his land was  described as "late of Thomas Bolle" rather than the property of his inheritors as stated in the 1466 grant below.

A grant from 1466 to Thomas Bolle (note: jr.) of Chartham parish refers to 1 1/2 acres of woodland at 'Trenhamme' in Chartham parish lying with Thomas' (jr.) land to the south and the land of the heirs of Thomas Bolle to the east." ref. Another grant from the same year to Thomas Bolle of Chartham regarding 4 acres of land at Trenhamme lying with the land of the heirs of Thomas Bolle to the north and states that Thomas held the land as the gift of the late Thomas Bolle. ref.  Note: a William Malvyle is a witness on both grants.

Chartham Manor was granted to a Bolles in 1457 with a Lease from the Prior and Convent of Canterbury Cathedral Priory to Thomas Bynge, husbandman of Thanington; Thomas Bolle, husbandman of Chartham; Henry Goodbacon, husbandman of Chilham; William Pette, husbandman of Chartham and Hamon Pope, husbandman of Godmersham.  ref.  This lease has to be examined to verify just which portions of the Chartham Manor were included as the summary refers to exclusions.  Most likely the manor house itself was not included as it would not as easily be shared by a group of investors as the land would and the Bolle's already had a great house, see the next entry.

A Will drawn up in 1459 for John Bolle, a grocer in London but who was born in Chartham refers to his "grete house at Shamelford' which would most likely refer to their house at Shalmsford which would later be called Bolle Hall.  From the Will we also know that his wife's name was Blanche with whom he had a son John; that he had a half-brother William; brothers Richard, Thomas and Henry and a sister Alice.  See John Bolle, Merchant of London

A lease dated Sep 24, 1476 is from the Prior of Canterbury Cathedral Priory to Thomas Bolle, William Bolle, junior, William and John Harry and William Bacsnorth for Chartham Manor with crops and stock as specified except for specified buildings, lands and rights for annual payments of £34, 21 quarts of wheat and 42 quarts of barley.  Another requirment was the keeping of records for the manor and for holding courts.   An undated lease from the same period mentions that John Bolle is bound by the same £100 bond as William Bolle of Chartham Manor.  ref.  The actual bond agreement is also available at the archives.  From that catalogue entry it would seem that William Bolle jr. may be underage as the other four are providing the £100 bond on William's behalf. All five are also stated to be tanners. ref.

A deed dated 1478 involves Thomas and William Bolle holding the Chilham Rectory under the ownership of Elizabeth, the Abbess of the Convent of Svon.  ref. 

A grant dated 1481 to Thomas Bolle, tanner, of Shalmsford for additional land in Trenham has witnesses William a Pette, William Harry, John Strongge and others.  It seems strange that Thomas Bolle who is holding court at the Manor would still be described as a tanner but it is likely that same Thomas Bolle as one of the witnesses is his co-leaseholder William Harry. ref.

Another bond from 1484 has William and John Harry and Thomas and William Jr. Bolle providing a £50 bond to William Selling, Prior of Canterbury Cathedram Priory, in support of their lease of Chartham Manor for one year.  ref. 

In 1497, William Bolle obtained an exclusive 7 year grant for Chartham Manor, except for specific buildings, lands and rights as specified and for annual payments of £10 and a quantity of wheat and barley as specified.  One of his conditions was to hold the manor court but I have not obtained the complete document to establish the full terms of his grant. The grant summary includes a comment that William Bolle, John Bolle and Henry Gosebourne were bound by a bond of the same date for 100 marks.  ref. 

A release by John Bolle of Chartham dated 17 Henry VII (1501) refers to his wife Joan, one of the the kinswomen and heiresses of William Moyle through William's sister Agnes Hovynton and cedes their interest in a tenement in St. Sepulchre without Newgate parish in the ward of Faryngton Without to the use of Robert Rede, knight.  ref. 

In a very badly damaged document dated between 1503 and 1511, William Bolle, tanner, releases some land in Trenham which had been inherited from his father Thomas Bolle (Sr.).  ref.  So both Thomas Bolle Jr. and William Bolle were tanners.

There are no later records in the Canterbury Cathedral Archives for Bolles in Chartham but that doesn't mean that there aren't more to be found yet.  Hasted wrote that the Bolle family became "extinct" at Chatham at the beginning of the reign of Queen Elizabeth I (1558).  The above last two documents being Releases may be an indication that the family was in the process of moving on.