No hotel in San Gimignano is cheap and, the town being so tiny, there are very few hotels within the town walls—which is why you should be especially careful of booking sites (and some guidebooks) that don't make this last point too obvious, attempting to foist off the glut of hotels in newer parts of San Gimignano built outside the ancient city walls.
The best of the hotels in the historic center include the following:
Hotel L'Antico Pozzo - Spacious rooms with iron bed frames and 19th century furnishings give "The Old Well" a wonderfully stony "ancient palazzo" vibe—and or good reason. This palazzo dates mostly to the 15th century, but parts of it are even older—those would be the bits that played host to, in different eras, the poet Dante, Inquisition trials, and a religious community. "Superior" rooms enjoy 17th-century ceiling frescoes; jr. suites come with canopy beds. Via San Matteo 87, tel. +39-0577-942-014, www.anticopozzo.com. Double rooms €110–€140. From €110 online.
Hotel La Cisterna - This oldest of Sangimignanese hotels, installed in the stumps of several interconnected 14th-century towers, has long been a favorite of movie directors (Where Angels Fear to Tread, Tea with Mussolini). Rooms on the front overlook the pretty piazza, with its ancient well and ring of towers. Rooms on the back have a panoramic vista of the quilted, classic Tuscan countryside of stitched fields and terraced vineyards rolling away beneath the town. The hotel restaurant is among the town's finest. Piazza della Cisterna, tel. +39-0577-940-328, www.hotelcisterna.it. Double rooms €80–€120. From €85 online.