Amy Slate's place is very nice. But are you talking about the Steeplechase or Tradewinds? Hard to tell since they got a little mixed together in this thread.

For the Steeplechase the rate at Gilbert's is $59 or $69, depending on whether upstairs or down. I would think all the Steeplechase sailors would want to stay at Gilbert's, since that is where the race finishes and there will be a barbecue after the races. But if you are staying at Amy Slate's, I assume you would be launching and pulling out at Rowell's Marina, so keep in mind that they close and lock their gate at 5:00 p.m. Could be a problem if the second day is light air.

If you are talking about the Tradewinds Regatta, I just talked to Amy Slate's place, and their lowest rate for that weekend is $100 for a double room. And, of course, you would have to pay to launch somewhere. Again, if you are staying at Slate's for the Tradewinds, I assume you would be sailing out of Rowell's Marina. (Gate closure time won't be a problem for the Tradewinds.)