It's complicated.

Across the Years in Pr. Geo. Co., MD, by Effie Gwynn Bowie:

Henry DARNALL (1564 - 1607) m. Mary BROOKE, d/o Wm.

Henry DARNALL was a Counsellor at Law, Gray's Inn, London. His tombstone at Essenden names children John, Henry, Sir Thomas, Susan, Anne, Philip, & Ralph.

Col. Henry DARNALL (1645 - Je. 1711) of Anne Arundel Co., MD (son of Philip of Henry) came to Maryland by 1672. He m. Eleanor [HATTON] BROOKE, b. 3 Apr. 1642, wid/o Maj. Thomas BROOKE of Brookfield.

Lib. BB3, folio 535, Annapolis, 1 May & 10 Sep. 1698: Mr. Clement HILL was directed to resurvey his Lordship's Manor, Portland Manor, Anne Arundel Co., 1000 acres for his Lordship's use and remainder (1009 acres) for Col. Henry DARNALL, granted 7 Dec. 1697, sealed with the Great Seal at Arms, 20 July 1699. Will of Col. Henry DARNELL of AA Co., pr. 17 July 1711, named son-in-law Clement HILL, husband of dau. Anne.

At Woodyard, aka Delight of the Darnalls: Hereby is interred the body of Col. Henry Darnall (son of Philip Darnall, Esq.) who departed this life 17 June 1711, in his 66th year. Widow Eleanor's will was pr. 21 Feb. 1725, AA Co., and named dau. Ann HILL.

Clement HILL (24 Feb. 1670, Taunton, Somerset - will pr. 25 Aug. 1743, Pr. Geo. Co.) came to Maryland in 1693 and lived with his uncle Clement HILL until Sep. 1696, when he m. Ann DARNALL (1680 - Mar. 1749). They had Clement (heir-at-law); John; Elinor, b. 1700; Henry, 1708; & Anne HILL, 1711. Will named wf. Ann & son Clement, coexs., sons John & Henry (& Henry's son Clement), dau. Elinor HOLLIDAY, grandchildren Sarah, Millicent, Elinor, & Mary BORDLEY.

Elise G. JOURDAN's Early Families of S. MD: Clement HILL & Ann DARNALL had dau. Eleanor HILL, who was the second wife of Marsham WARING, whose will was pr. 20 Oct. 1732. Eleanor m2. Leonard HOLLIDAY & m3. Dr. MURRAY of Cambridge, MD. Basil WARING (1711 - 15 Apr. 1793) s/o Marsham & Henrietta, m2. ca. 1753, Susannah DARNALL (ca. 1723 - 19 Jan. 1786), d/o Henry DARNALL.

Henry DARNALL of Portland Manor, AA (of Philip, Henry, Philip, Henry) m. Elizabeth LOWE, dau/o Col. Henry LOWE & Susanna [BENNETT] DARNALL, dau/o Richard BENNETT, widow of John DARNALL. This Henry DARNALL's dau. Ann m. Leonard BROOKE.

Clement SMITH (1718 - 1792, s/o Walter SMITH & Susanna BROOKE) & wf. Barbara SIM (dau/o Patrick SIM & Mary BROOKE--so Clement & wf. Barbara were cousins) had son Clement SMITH, Jr.

Clement SMITH (ca. 1760? - will pr. Dec. 1831) m. ca. 1786, Ann DARNALL, b. ca. 1766. Indenture of 14 June 1790, Lib. JJ:2:84, between Addison MURDOCK, Pr. Geo. Co., & Ann Darnall SMITH, wf/o Clement SMITH, "Bowdle's Choice," Pr. Geo. Co. [land description is in Across the Years in Pr. Geo. Co.]

Clement SMITH & Ann DARNALL had

Ann Darnall SMITH (1787 - 1823) m. 9 Dec. 1811, Wm. HILL, b. 12 Jan. 1783.
Catherine SMITH, named SMITH in father's will.
Barbara Sim SMITH (1794 - 1862, D. C.) m. 30 Jan. 1814, Pr. Geo. Co., Ignatius Fenwick YOUNG (29 Dec. 1790 - Feb. 1834)
Mary, m. 20 Apr. 1830, Pr. Geo. Co., Notley YOUNG.
[Father's will incorrectly names dau. Barbara instead of Mary as wf/o Notley. Marriage records are online.]

Do you have dates and places to identify the Ann BROOKE & Eleanor HILL mentioned?