In 1908, when she was 65, Jekyll was asked by Charles Holme to design the garden for one of his houses at Upton Grey in Hampshire. Holme was, by then, an established figure in the Arts and Crafts movement. He had founded The Studio magazine in 1893 and subsequently edited it. The Studio was undoubtedly the most influential and widely read magazine of its kind in the world. Holme had extended his family's woollen and silk business to the Far East and was one of the founder members of The Japan Society, a country whose art he admired greatly . Holme moved to Upton Grey in about 1902 from the house that Philip Webb had built for William Morris, the Red House,in Kent. Holme purchased several houses and a great deal of the surrounding land in Upton Grey. The Old Manor House, which he rented out for the rest of his life, was in fragile condition, so Holme commissioned the local architect Ernest Newton to alter and adapt it, keeping many of the original timbers - those in the roof are dated between 1480 and 1540. Today's Edwardian façade encloses oak-panelled rooms, a 16th century staircase and the original roof timbers. Newton's house was completed by 1907.

Gertrude Jekyll drew plans for the four and a half acre garden. On this chalky, sloping site she designed one of her most beautiful gardens. It includes many features of a typical Jekyll garden, but on a rather smaller scale than most of her commissions.
To the west of the house stands the Wild garden. Grass paths wind from semicircular grass steps through rambling, species roses, to a small copse of walnut trees and wild flowers, beyond which lies a small pond. Some of Jekyll's original drifts of daffodils remain at the end of the Wild Garden, still in the drifts she designed. To the east of the house stands the formal garden. Here there are no curved lines. In a geometric outline Jekyll designed a Rose Lawn and typical herbaceous borders whose colours run in drifts from cool (blues and whites) to hot (reds and oranges) to cool again. These, with the tennis and bowling lawns are enclosed in yew hedging.