Typified by exquisite plaster ornamentation atop columns which appear to scrape the sky, The Cavalier's Jeffersonian inspired architecture was designed in the spirit of Monticello, with nods to locations such as Woodlawn, as well as The Lawn at the University of Virginia.
Influences derived from notable architects and historical places are, in and of themselves, some of the most remarkable aspects of the architecture of this grand hotel on the hill. James Gibbs, and his work at places such as the Church of St. Mary-Le-Strand at Aldwych in London, inspired the decorative water tower which crowns The Cavalier.
The plaster ceiling in the Rotunda lobby was inspired by the ceiling in the Moses Myers House in Norfolk, while the terrazzo floors and old pine wood trim were meant to invoke Colonial era homes. This is also true of the landscape design; which was specifically planned to conjure up musings of the early Virginia plantation houses of Shirley, Brandon, Yorktown and Westover.
These influences extend to the serpentine walls, tall posts, sloping front lawn, sunken garden and brick walkways at the grand entrance of The Cavalier.
The hotel building is constructed in a "Y" with the long leg of the building extending east toward the ocean and reaching seven stories in height, while the two branches of the hotel extend northwest and southwest and are six stories tall. The exterior of the hotel is Flemish bond brick with numerous cast stone decorative elements. There is a belt course with dentils between the fifth and sixth stories as well as a classical balustrade along the roofline.
Iconic pilasters link the cornice to the balustrade along the eastern end, while alternating quoins highlight the corners and link the cornice with the balustrade on the two wings.The corners are capped at the roofline by decorative capped piers which echo the piers at the Cavalier Drive entry.
The upper façade of the hotel facing the ocean features a classical temple format on the top two levels with the quoins and two central pilasters echoing the entry pavilion on the north end. There is a pediment filled with the familiar garland and swag theme along with a heraldic type shield element.
The center of the roof features the large Water Tower with four finished sides featuring triple arcaded windows, which echo those along the entire first floor, and a pediment highlighted by a round cast stone element. The hotel is topped by a cast stone cupola serving as a bell tower and features round arches, pilasters at the corners and a copper roof. There is also a large brick chimney abutting the interior of the northwest wing of the hotel.
The main entrance on the northern facade features a classical four-column portico inspired by the east portico of Monticello and accessed by three stone steps. The columns are smooth and capped with Egyptian styled capitals. Above each column in the cornice is a garland and swag element, and the pediment is pierced by a round window surrounded by undulating plaster elements.
Under the porch is an arched entryway with a central pair of doors and paired single doors on the two sides. A twelve-over-twelve double-hung sash with cast stone sills and lintels flank the entry doors. Above theses side windows are two stone reliefs which also feature garland and swag elements.
The arched entry window and doors are echoed around the three public sides (north, east, south) by a nearly continual arcade of windows behind which are the swimming pool, porches and verandas.
Each corner of the first floor has a single bay entry pavilion with an arched entry, simple pediment and a domed copper roof.
The windows on the rest of the building, serving the individual rooms, are six-over-six double-hung wood sash with cast stone sills for the bedroom and small one-over-one windows for each bathroom. The two shorter rear wings are eight bays long, while the longer ocean side main leg is 11 bays long.
Now gone to make way for the newly erected Cavalier Residences, there were many pines and cypress planted around the hotel, inspired by Magnolia Gardens of Old Charleston, South Carolina.