Prospect Hill – The Virginia Plantation Inn,
Bed & Breakfast Inn and Restaurant



Prospect Hill Plantation Inn & Restaurant:
A Romantic Charlottesville Inn

Authentic Charlottesville,
Virginia Plantation

Once an authentic 18th century plantation, Prospect Hill was long-ago transformed into a premier Charlottesville, Virginia area bed and breakfast. Between the Manor House and the nine original dependencies (circa 1699 – 1850), we offer eleven distinctively individual guest rooms and cottages. To call them unique would be an understatement - by keeping each cottage’s original function as intact as possible, our accommodations vary from elegant to rustic. All, however, are packed with character, brimming with history, and tell a purely Southern story of folklore and tradition. With private baths, working fireplaces, creaky floors, expansive views, private decks, and incomparable romantic charm... each room defines who we are and tells the story of Prospect Hill.

Located in a Beautiful Blue Ridge Foothills Setting

Nestled on 40 pastoral acres and situated at the foot of the Blue Ridge Mountains, the award-winning grounds at Prospect Hill are magnificently beautiful, with many of the original 1840’s tree plantings (including the rarest magnolia species in the U.S.) forming a 5-acre arboretum. Whether reclining under the pool's shade pavilion, reflecting by the garden gazebo, strolling the expansive grounds, or hand-feeding horses, sheep, and chickens, the magic of Prospect Hill will make leaving difficult... and returning a near necessity!

The History of Prospect Hill

Western Frontier, The Beginning

Our story (more than you want to know) begins in the late 1600’s... As one of the first settlers in central Virginia (then known as the Western Frontier), Roger Thompson selected a home site atop a hill and proceeded to build a 10’ X 10’ log cabin. Though simple, it served his needs well. After several tough years, just as he was beginning to experience farming success, he became engaged to the widow Mary English. Mary brought her deceased husband’s wealth into the marriage, as well as several sons. Suddenly cramped for space, Thompson built a larger cottage beside the original cabin. He and Mary lived in this second cottage while their sons stayed in the original cabin (still referred to as “The Boy’s Cabin”).

By 1732, the Thompson family had grown to include 13 children, necessitating the construction of a larger manor house (the parlor windows still have the hand-blown panes with their wavy, irregular swirls).

A Plantation Begins

Following the death of Roger Thompson in 1739, Prospect Hill eventually passed to his relative, Richmond Terrill and his wife, Sally Overton Terrill. As the farm continued to prosper (by now it was 400 acres), the Terrills introduced slaves to work the fields and Prospect Hill grew into a full-scale plantation (where others, instead of the planter, worked the fields). By the 1800’s there were about 20 field-hands living in the original slave quarters (now known as “Uncle Guy’s House”, after the slave foreman who once lived there). As absentee owners, the Terrills grew tired of the responsibilities of Prospect Hill and conveyed the home to Sally's half-brother, William Overton and his wife, Martha Gilliam Overton, in 1840.

The Overtons quickly expanded the manor house, adding an east and west wing, including a dining room and ballroom. Here, three generations of Overtons would live (until the last one would pass away in 1969). Due to the successful transition to wheat farming, the Overtons extended their wealth by exporting this high-quality staple to Europe in the 1840’s and 1850’s. They in turn acquired more land, as well as the slaves to work it. Additional outbuildings were constructed at this time, including the Carriage House and its upstairs slave quarters, the Grooms’ Quarters.

The Civil War Years

The Overton’s son, William G. Overton, Jr., graduated from Virginia Military Institute in 1859, and was commissioned a Second Lieutenant in the Provisional Army of Virginia on May 1, 1861. He served under his former VMI professor, Gen. Thomas “Stonewall” Jackson, and as a member of The 1st Battalion, of The Army of Northern Virginia, under General Robert E. Lee. Overton participated in almost every major battle fought in Virginia, including the battles of Cheat Mountain, The Shenandoah Valley Campaign, Cross Keys and Port Republic, Cedar Mountain, Second Manassas, and Antietam (Sharpsburg), when he was promoted to Captain and transferred to Lee’s Headquarters as Provost Guard. Overton would eventually serve in every remaining battle with Lee until the surrender at Appomattox Court House. Overton and his newly-freed slave, Sanco Pansy Scott, walked barefoot to Prospect Hill after his pardon on April 9, 1865.

In December, 1874, the junior Overton married Nannie Branch Giles, the granddaughter of Virginia Governor William Giles (a contemporary of Thomas Jefferson). Nannie had also joined the Confederacy and was a bill-signer at the Confederate Mint in Charlotte, North Carolina during the war. She assumed responsibility for the household accounts and quickly realized that, in part due to the terrible economic depression in the South, Prospect Hill was losing a great deal of money on farming. Consequently, Nannie in 1874 began selling tracts of land and accommodating overnight guests from Richmond, Washington, and other eastern cities. About this same time, Nannie would inherit a home in Washington, DC from one of her relatives, General Giles (who refused to resign his US commission following the war and remained in the Union Army; his ongoing wearing of his uniform did not please Overton and became a thorn in their marriage). With this newly-inherited home, Nannie, along with her daughters Frances and Marcie, opened a boarding house. From here, these ladies catered to women who worked for Congress, bringing them home to Prospect Hill during Congress’ summer recesses.

The manor house was later expanded with two more bedrooms, a pantry, and the addition of the kitchen. The business of innkeeping gradually faded in the 1920’s as the economy soured, and Prospect Hill served as a private residence until the deaths of Miss Frances (in 1957) and Miss Marcie (in 1969).

Prospect Hill - The Virginia Plantation Inn Today

Following the sisters’ deaths, Prospect Hill changed hands several times, until the Sheehan family purchased in 1977 and began extensive renovations... improvements which would place it on the National Register of Historic Places and the Green Springs National Historic District. Innkeeping was restored, and Prospect Hill Plantation Inn & Restaurant garnered national attention for its award-winning fine dining. Upon the Sheehan’s retirement in 2012, Prospect Hill was purchased by Dr. Bobby and Paula Findley (and their five children). Once again serving as a home to a family, Prospect Hill now bustles with activity while offering a quiet refuge from the city with emphasis on excellent food and genuine Southern hospitality.


Full Gourmet Breakfast
(in bed, if you wish!)

Complimentary Wi-Fi
(Manor House common areas)

Elegant Parlor
(with baby-grand piano, fireplace, board games and books)

On-Site Complimentary Parking

40-acre Grounds
(with manicured gardens and
ancient boxwoods)

Swimming Pool
(with covered shade pavilion)

Hair Dryers, Irons, Ironing Boards

Elegant Fine-Dining Nightly
(reservations required)

“Select Registry - Distinguished Inns of America” (founding member)

Niche Wine List (award-winning selections from our cellar)

Dogs, Cats, Hens, Alpacas & Horses
(No Lions, Tigers, or Bears, oh my)

Two Historic Cemeteries on Grounds

1840’s Grand Ballroom with Fireplace (meetings, receptions & retreats)

Large Garden Gazebo (weddings, proposals, artists & writers)

Nature / Walking Trail

5-acre Century-Old Arboretum

POLICIES: Please read before making your reservation. Click Here

I stayed in the 1850 Carriage House and had the best time ever! I suggest you have dinner at the plantation as the chef/ambiance is unsurpassed. The pool was fun for a quick dip. Breakfast was scrumptious and filling!”
Yelp (January 2016)

“Love this place! Chef is amazing, staff most delightful, room was warm and inviting. Looking for relaxing and peaceful spot - THIS IS IT!!”
Google (September 2016)

“Such a luxurious stay. We felt welcomed and pampered. Dinner in the restaurant was also first class!”
Google (July 2016)


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