We were there in late October 3 years ago and fell in love with HH. The weather was generally nice, but a few days were overcast, breezy, and cooler. We didn't really enjoy the ocean on those days, but the pool was warm. We also had a couple of spectacularly sunny and quite warm days with a very mild breeze. We walked and walked the beach and marveled at how clean and beautiful it was there. We heard from friends that there was a better chance of consistently warmer weather in early Oct. I just 'waded' in the ocean because I can't swim strong enough to go in very far.
We had our choice of plenty of great restaurants, and also enjoyed lots of shops. Hope you have a great trip!
Edited to add that we would definitely go back again in late October if we couldn't schedule a trip earlier in the month.