Definitely start with these:
http://www.dansdeals.com/archives/2581http://www.dansdeals.com/archives/2738Here's some more info:
-I'm going with the assumption that you are using Starpoints-(if not, why are you only looking at Starwood hotels?)
-As far as I know, the only Starwood in Israel with mehadrin food is the Sheraton Jerusalem.
-If there are no (2,800+$45) Cash and points awards for your dates at Sheraton Jerusalem you should use a 5th night free or nights and flights award.
-Sheraton Jerusalem is very walkable to the old city and kotel. I didn't eat shabbos meals there but they are probably a good option if you don't have friends/relatives there. There's so much to do here that you can't spend enough time based in Jerusalem.
-Artzeinu has a nice tour of Chevron/Kever Rochel that leaves from the Sheraton with an armed guard and bulletproof bus.
-You can spend a day in Tel Aviv while still sleeping in Jerusalem very easily.
-The breakfast at the Sheraton Jerusalem is $10/person if you're staying with points. I'd say it's worth it just for the convenience alone.
-Sheraton Tiberias makes a great launching pad for Tzfas and the Golan and all of the kevarim in the north. Definitely worth a few nights.
-Le Meridian Haifa is definitely worth a night-just book 2 nights and have Starwood cancel 1 out. Other Starwood hotels in Israel play the minimum stay game as well with weird restrictions, just book what they want you to book and cancel what you dont want, you won't have a problem.
-Le Meridian dead sea: 1 night is plenty here. The Dead sea takes just a few minutes to experience and is sure to reveal every scratch on your body. Ein Gedi is nice, but many golan hikes are nicer. The Metzdah light show is pretty cool, but only runs on certain nights, and you have to take derech arad to get there from the back end.
-Eilat is hugely overrated. Maybe this is because I was there in August, but it's got absolutely nothing on places like Hawaii. Rocky beaches and subpar snorkeling don't justify the drive down IMO.
We stayed at Herod's palace and got a mind-boggling SPG gold upgrade that made the long trip down to Eilat worthwhile, but alas Herod's is no longer part of Starwood.
The mehadrin restaurants, pizza lek and the felafel at felafel tubal are well above average.
If you do go down check out timna park on the way.
Oh yeah, getting an Egyptian passport stamp was actually very cool, and with an American passport you should be able to sweet-talk the Israeli border control into waiving the departure tax.
OK,that's enough for now...more to come bl"n.