if you need health insurance, use harel - it's an israeli company. they're great. reliable and cheap. google 'sasson chacoty harel' and it should come up..it's $1 per day per person and includes dr, er visits and meds too in the event it's necesary (G-d forbid).
as far as up north, you have many options...if you want mystical go for tzfat - you can try the rimonim though it's not mehadrin...no worries there are plenty of eateries nearby
if you want more classic, try nir etzion near haifa or kibbutz lavi
keep in mind that many hotels have 2-3 night minimums during peak seasons.
enjoy!