Dining there has many options. Room with a View right at the Castle is very good and there is a pool bar/grill. I liked Thirteen on the north side, make a reservation and get directions. Mimm's for Thursdays all you can eat shrimp night, go early to enjoy the water view or any night is no doubt good. Downtown Greenhouse is a fun lunch. Epernay in Frenchtown is a small wine bar with a few tables, good food. Sib's has a terrific Sunday sandwich the Godfather and the ribs are good too. Had a nice lunch/dinner at Fat Turtle which is in the new section of shops near the harbor/ship dock. East end Latitude 18 has good food in a very casual place with music in high season. We had good food in XO in Redhook , same stip mall Duffies Love Shack is.
For cost the dining out compares to going out here at home in a decent place.