Loches, which I find a rather gray grim-looking city, has to me one of the best castles and one that is really a fortified castle and not a pleasure dome built more for looks than defense. And this is where one King Looie, I believe that was his name, hung out for years - literally in one of the famous Hanging Cages in the dark dungeon - in a cage too small to stand up in if I recall rightly.

There are many many places in the countryside - in smaller chateaus that offer the lazing by the pool and provide bikes for guests, etc. Lots and lots of them. And there are many B&Bs as well dotting the rural roads and farmstays, etc.

Another vote for Le Vieux Manior in Amboise. We stayed in the least expensive room, Madame du Barry, and were very happy. The view was lovely, breakfast excellent and the hosts very welcoming and interesting. When we arrived they took our bags up to our room and invited us to a wine tasting in the cellar. We were there in late September and the weather was cool and it was not overrun by tour busses. We could walk to dinner each evening and had an easy time navigating to sights in the Loire. Don't miss Bigot below the Amboise castle for tea and pastries.

"There are many many places in the countryside - in smaller chateaus that offer the lazing by the pool and provide bikes for guests, etc. Lots and lots of them. And there are many B&Bs as well dotting the rural roads and farmstays, etc."

Exactly why I'm finding this to be so overwhelming. I've spent hours every day for more than a week reading books, websites, and travel forums trying to figure this out.

This is a larger, lower-priced hotel that we considered before selecting Le Vieux Manoir a few years ago as I mentioned. They are on the same road. We chose Le Vieux Manoir based on the recommendation of an acquaintance but thought this looked good and is within your price range.
http://www.leclosamboise.com/AtmosUK.asp

I often over-research (I'm a librarian!) destinations and have already bookmarked dozens of hotels and sights for our fall vacation. I understand the diffculty.