We'll be spending 5/28-5/31 doing a loop around Madrid and will be perfectly happy in clean & simple lodging in small towns in the Aranjuez- Chichon-Toledo area or maybe in the Avila-Sierra de Gredos area. Is there normally something available or am I foolish not to reserve? We really wanted to just wing it rather than be locked into a certain schedule.

Be aware that you´ll be in Madrid and its environs during the monthlong bullfighting feria of San Isidro and lodging is often hard to find. But if you´re not picky or don´t mind a few "turn-aways" you can probably find something eventually, doing a little extra leg-work.

Good luck! Saludos, MadridMan