Showing holiday shipping cutoff dates on your web site makes sense for many reasons. First, it sets the customer’s delivery expectation. Second of all, it will reduce the number of calls you’ll get asking if an order will be delivered by the holidays.
You should show this information in 2 places — the homepage and in checkout. I typically favor a rather prominent link on the homepage to a dedicated page that discusses holiday shipping. In checkout, you’ll want some messaging saying something like “Order by December xx to ensure holiday delivery.”
One thing we do effectively on the Virginia Favorites site is to list the estimated shipping date on every product page. This, combined with the holiday shipping information that lists cutoff dates, helps the customer determine if their order will arrive in time.
