No it doesn't hurt to ask but the calendar is up to date 99% of the time.
You say it sleeps four but I only see one bedroom: Yes, the cottage is best suited for parties of two. But there is a full sized futon in the living room that can be used as another bed.
Limit of 4 persons & 2 pets: Sorry no exceptions.
Is the cottage on the water or can you see it: Only from the top of the driveway in the winter with the leaves off the trees . The water is 1/2 mile straight down the road. It's a nice walk or bike ride.
Do you rent daily: Yes, we do have minimum but generally during July and August we won't take a reservation for less than a week until 2 weeks before the requested arrival date. If you would like to be notified of availability via email then click the email link to the left and fill out the short form.
What other fees are there: Unlike many sites we do not now or later add on any other fees. The rates you see are what you pay. They are outlined in full on the reservation and payment page.
When will I get my security deposit back: Assuming everything is in order after you leave, most people get their security deposit back within the first 3 days but I am human so if you haven't recieved it in a week email me.
Will we meet you: I live about 100 yards away and do try to at least say hi, introduce myself and answer any questions, so yes most likely.
Is it available during the winter: No, depending upon the weather and business I usually close it up and winterize the cottage around mid November.