Cunningham's Country House Restaurant has high local significance as a key landmark township building until recently owned by Karl and Patricia Cunningham, who hold an historic wine licence, the second oldest in Victoria issued to the Paul family in the 1870s. It is the oldest wine licence in the Yarra Valley. The Pauls, who owned and occupied the present building before the Cunninghams, owned two earlier "wine shops" or "wine halls" at other locations in Yarra Junction township.

Cunningham's Hotel is a distinctive landmark within Yarra Junction township. Although there is said to be some evidence of the earlier wine hall remaining within the complex, the buildings that are visible today appear to date from the 1920s or later. Further detailed examination may be warranted at a future date regarding this earlier evidence.

The building is a gable-roofed structure possibly constructed in several stages. The eastern end of the building is largely domestic in form, adopting the double gable typical of the Californian Bungalow style. The detailing is similar at the opposite end of the building however the main feature is the two-storey section in the middle of the hotel. This section comprises a large verandah level, now enclosed. The detailing on this section is quite fine with paired timber posts extending from the lower verandah through to the upper verandah. With the associated brackets, this verandah detailing presents a strongly Japanese appearance.

The verandah balustrade is clad in vertical black and white boards and this treatment extends to all of the gabled sections. This may be a later detail.

The main entry has flagstone steps leading under a small gable, through double front doors with 9-paned upper sections into the main rooms of the hotel. Internally the building appears substantially intact. A detailed inspection was not undertaken, however there are few examples of intact 1920s hotel interiors remaining in Victoria and detailed assessment of this interior would be worthwhile.

Physical Conditions: Good

Integrity: Minor Modifications