We have stayed at Hotel La Cisterna several times and loved it. The views from the hotel are wonderful. They have some sort of discount at the garage closest to the main gate but a cheaper alternative is the lot on the north side of town for about 10 euro a night, I think. You are able to drive up to the hotel btw to drop off bags through a gate around the back of the Town past the parking I mentioned above.

Have stayed at L'Antico Pozzo for 1 night as a treat for our anniversary a few years back. Lovely atmospheric hotel.

I would recommend staying within the city walls and paying the little bit extra for parking.

The Hotel Sovestro 2 KM out of San Gimignano is where my wife and I have stayed for the past 7 years each summer. It has a great pool, restaraunt, and view. The staff is very helpful (The girls speak English, Sergio (the father is still struggling!). They have a great buffet breakfast, and afterwards we walk it off by taking the gravel road to town, walking around the entire town and back to the hotel. It takes an hour, but the scenery and exercise are well worth it. The price is about 110 EU for a double with breakfast.

We love that area of Italy. We stay there about 10 nights per summer and take day trips to Siena, Castelinna in Chianti, Volterra, Assissi, etc.

Take a look at Hotel Vecchio Asilo outside of San G. It's a few km but the drive is very easy. We stayed there for 4 four days in May and loved it. Guido speaks English and he and his family take wonderful care of you. The breakfast is wonderful and the rooms are spotless and they even have fresh flowers for you in the room. It a great value also. It's rated one of the top ten for best value. Unless you really want to stay inside the walls, I highly recomend this place.

tripadvisor.com/ShowUserReviews-g187901-d238…

Above is a link to my review of the Leon Bianco, located in central San G. Awesome place to lay your head.

Seeing this question I thought to myself, "wonder if anyone stays at la Cisterna anymore?" and it's good to read that people do. We haven't stayed there for yonks (for which read 16 years!) but have very fond memories of a lovely few days, and we've certainly eaten there since often. Obviously can't comment on the rooms, etc nowadays but the fabulous view can't have changed, the location is ideal and the food is reliably good.