5 best countryside hotels in San Casciano Val Di Pesa

Countryside hotels in San Casciano Val Di Pesa put you right on the edge of Florence’s Chianti landscape—an area of hill villages, churches and vineyards that’s just over 15km from the city centre. The town itself is a medieval hill settlement, often described as a “Florentine” gateway to the Chianti hills, so countryside stays here feel genuinely rural rather than remote.

For travellers, this is ideal for couples and small groups who want a slower pace: expect agriturismo-style settings, countryside views, and a base for wine tastings and day trips without spending time commuting all day. It also suits food lovers and hikers who prefer village-to-village exploring around local pieve and valley paths—such as the network of historic “pievi” documented by the Comune.

Where to stay is simple. Choose the San Casciano historic area if you want an easy walk to local sights and restaurants, then drive out for the vineyards. Alternatively, opt for the outlying countryside hamlets/frazioni (vineyard estates and farmhouses), which best match the “countryside” promise—great for quiet stays at a villa or agriturismo.

From our inventory, options include Agriturismo Macinello (high guest score), Borgo Montefolchi (3★) for a more structured country base, and smaller rural choices such as Villa Del Mughetto (1★) and Pergolato di Sotto (1★) for straightforward countryside accommodation.