SkaiSW

I decide when to go based I want to see.
I check
http://www.insidervlv.com/entertainment/showrooms.jsp
http://www.lasvegas-nv.com/showsh.htm

For example, Fleetwood Mac was just there and three Dog night is there only on Sep 6. Or you might want to see Elton John or a particular comedian. For hotels, I like the Mirage. I just submitted a trip report called "Las Vegas Trip Report (for non-gamblers)" that might give you some ideas. I enjoyed writing it, and hope you will take a look at it.
If entertainers are secondary, another strategy would be to call all the better hotels: (Wynn/Encore, Venetian, Bellagio (owned by MGM) and Mandalay Bay (also owned by MGM) and ask when you best can take advantage of promotional room rates.

crefloors

I think Elton John's "run" is over. If you are on the east coast and haven't been to Las Vegas, and probably won't go again, or won't go for a long time, I'd try to stay at one of the nicer places, Wynn, Encore, Venetian, Ceasar's Palace etc. I think if you can get a decent rate, it would be worth it and add to your experience.

Keep in mind it is a long way between hotels, even if they are next to each other. They are so huge and the grounds are so big that there is a lot of walking involved so take good shoes. Also, there is a lot of hard surface floors, tile marble, so you legs can get pretty tired.

Little_Man

I've stayed at Palms Place, the Palms new condo/hotel. Very hip, and chic -- their 1200 sq. foot 1 bedroom suites are something else, especially if you like very modern decor. We got an amazing rate on one about a year ago ($199) a night. It's not walkable to the strip though, and for me, the MGM Signature, another condo hotel, is even more comfy, and
better located.

SkaiSW

The Palms is not on the strip. This is a BIG deal. I strongly recommend that you stay on the strip. I like the Mirage.

SAnParis2

Do people really spend time in their rooms when they are in Vegas ?? I don't get spending a couple of hundred bucks on a room that you rarely use (of course I typically get comped). Still....

Little_Man

I do!!! Their's a lot of fun in hanging out in a swanky room with your romantic other...! And Vegas has great rooms at great prices, and there's so much to do. It's actually a great romantic getaway spot!