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It's quite noteworthy that there are relatively few
hotels in Chianti, in part because Chianti is a rural area with few
towns of more than 10,000 inhabitants. Each the five
main towns of Chianti has at least one hotel but visitors may well be tempted
by the villa hotels in the countryside. These are historical
villas that have been converted into boutique accommodation,
usually preserving the characteristic features of the classic Tuscan
villa. Farmhouses (case coloniche) are the main
form of vacation rental accommodation in Chianti, Italy. Many
websites and individuals refer to Chianti farmhouses as
"villas" purely because they are stand-alone
structures. In addition, many Chianti farmhouses have been
divided up into self-catering holiday apartments.
Another great form of accommodation in Chianti are Bed and Breakfast
establishments. B&Bs can be found in the Chianti towns and villages but wine estates also offer
this form of vacation lodgings. Another way of distinguishing
among the villas, farmhouses, apartments and B&Bs of Chianti is
to divide them into true Chianti
agriturismi, meaning working agricultural concerns (fattorie,
almost invariably wineries and/or olive oil producers), on the one
hand, and all other rural holiday rental accommodations, on the
other. There are a few Chianti farm stays where children will find
farm animals to look at and sometimes to play with. 
Here are some links to a selection of hotels, holiday
villas, apartments and B&Bs, mostly in the Chianti region
but with some also in other interesting parts of Tuscany. All
of these properties are known to me personally and they are
all owner-direct reservations (i.e. no price markups).
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