Here is a different approach. Don't stay in Times Square. Stay in an elegant residential area. The restaurants are better and the museums, etc. are around there. You can always take a cab to Times Square anytime you want and if you are traveling with an older relative it is more peaceful. In that vein check out the Hotel Wales around 90th and Madiso. Not a "posh" hotel but very nice, quaint, reasonable (for NYC) and it's room service comes from a wonderful restaurant in the building - Sarabeth's for those who are familiar with that name. It is much more civilized up there and closer to the Metropolitan and Whitney museums among others. It is one of the hotels on the Upper East side where permanent residents check in when their homes are being renovated and it is implausible to stay in them. My 2 cents.