There are many places to stay in the Chianti region that are less expensive. San Gimignagno, not far from Monteriggoni has some lovely hotels, we stayed there 5 years ago for 5 nights and used it as a base and were able to see a fair bit of the country side. As well from what I have heard and read, around Siena, also not far from Monteriggoni, there are many places - Karen Brown's book - Inns and Itineraries in Italy has some lovely places.

Last year we stayed just outside of Cortona at Locanda del Molina (from Karen Brown) it was just over $100 Canadian dollars and had a wonderful breakfast and an even better dining room for dinners that were wonderful and a good value.

Good luck with your travels

Carol Toronto, Canada