I just spent the weekend in Healdsburg with a good friend of mine. We were headed up to attend an wine club event at Medlock Ames. Since we were both going to be drinking, we thought it best that neither of us drive home afterwards. Plus, we thought it would be fun to spend the night in Healdsburg!
We soon realized however, that most hotels in wine country require a two night stay, not to mention they are VERY EXPENSIVE. We almost decided against staying until I saw that there was a email contact at the hotel we wanted to stay at. I exchanged a series of emails with the hotel and in the end we ended up not only getting a room for just the one night like we wanted but we also got them to give us a discount on the room!
Now we did make the reservation rather late and we were off-season so I am sure that this benefitted us however we both learned that it can't hurt to ask. In the end, we had an awesome time in Healdsburg and an amazing hotel for a fraction of the price and for just the amount of time we wanted.