[5] Anne Clifford was brought up in an almost entirely female household—evoked in Emilia Lanier's Description of Cookeham—and received an excellent education from her tutor, the poet Samuel Daniel.

[8] On the death of her father on 30 October 1605, she succeeded suo jure to the ancient title Baroness de Clifford, a barony created by writ in 1299, but her father's earldom passed (according to the patent of its creation) as was usual, to the heir male, namely his younger brother Francis Clifford, 4th Earl of Cumberland (1559–1641), to whom he had willed his estates.

In her young adulthood, she engaged in a long and complex legal battle to obtain the family estates, which had been granted by King Edward II (1307–1327) under absolute cognatic primogeniture, instead of the £15,000 willed to her.

[17] By her first husband Anne had five children, three sons who all died before adulthood and two daughters and co-heiresses: Secondly, in 1630, Anne married the wealthy Philip Herbert, 4th Earl of Pembroke and 1st Earl of Montgomery (1584–1650), whose first wife, Lady Susan de Vere had died the year before.

Both marriages were reportedly difficult; contemporaries cited Lady Anne's unyielding personality as a cause, whilst her cousin Edward Russell, 3rd Earl of Bedford, compared her to the River Rhone.

[citation needed] A list or catalogue of the household and family of the Earl and Countess of Dorset at Knole survives.

It includes two African servants, Grace Robinson, a maid in the laundry, and John Morockoe, who worked in the kitchen.

[20] Lady Anne frequently went to London and the court, in November 1617, wearing a "green damask gown embroidered, without a farthingale".

[23] Clifford sent Lady Ruthin an expensive ruffled satin skirt with £100 worth of embroidery to present to Anne of Denmark.

[24] For a New Year's Day gift in January 1619, she sent Anne of Denmark a cloth of silver cushion embroidered with the Danish royal arms and embellished with slips of tent stitch.

Jan van Belcamp painted a huge triptych portrait of Anne Clifford to her own design and specifications.

Anne sent a miniature portrait of herself to her mother the Countess of Cumberland in June 1615, writing, "I have sent you my picture done in little, which some says is very like me, and others say it does me rather wrong than flatters me, I know you will accept the shadow of her whose substance is come from yourself.

After inheriting her father's estates in Westmorland, when the remaining male heirs (her uncle and his son) died out, Lady Anne thus became a wealthy landowner.

She was loyal to the Crown during the Civil War, defending her estates until they fell to the Parliamentarians after the Battle of Marston Moor.

[31] She was heavily involved with her tenants to the point of filing lawsuits against them and actively pursuing rents and debts owed to her.