Inhabited these lands were still in the old days. At present the city found the settlement of Scythian and ancient times. Over time, the edge went to the Galicia-Volyn principality. More than 100 years it dominated the The Golden Horde. After winning in 1362 the Lithuanian Grand Duke Olgerd army over the army of Tatars, skirts came under the power of the Lithuanian principality. Nephews, Prince Theodore and Constantine Olgerd Koryatovicha began to build on these lands walled city.
Among them was the Vinnitsa. This was first mentioned in documents in 1362. The first castle was built on the highest point of the left bank. In 1558, in order to gain protection against enemies built a new fortress on the island Kemp. Vineyard officially became a city in the XV century. In the second half of XV century enjoyed the Magdeburg law (letters were burned in a fire at the castle in 1580, restored in 1640).
In 1569 the town became part of Poland, from 1598 – Center Bratslav province. Vineyard has taken a prominent place in the War of Independence in 1648-1654. July 7th, 1648 rebels led by Colonel Maxim Krivonosov released from Vinnitsa Poles. Under the terms of the armistice in 1649 Zborowski Vinnitsa was included in the number of cities where Bogdan Khmelnitsky kept his garrison. In early 1651 the Poles broke the truce and invaded Podolia. March 11, the siege of the troops of the Crown Hetman Marcin pole Kalinowski. Three thousand garrison under the command of Ivan Bohun were repulsed several assaults. Soon on the besieged regiment came to Uman Josip deaf and Poltava regiment Martyn Pushkar. The Poles retreated, but were overtaken in the pursuit Yakushinetskom woods near Vinnitsa and defeated. On Armistice Andrusovo 1667 Vinnitsa, as well as all territory west of the Dnieper in Ukraine, has remained under the authority of the Polish crown.