Ask the Cheapos: Booking 25 rooms in New York City

Q: My wife and I are planning our daughter’s wedding in New York City this fall. We’ll have about fifty people traveling to the city for the occasion. Should I book 25 rooms myself or ask everyone to be in charge of their own reservation? – Steve K, Bellevue, Ohio

A: Good question, Steve! Planning a wedding in New York is already quite a project, and you probably aren’t in the mood to tackle reservations for 50. But there is a payoff to booking a group.

An “every man for himself” may initially seem easier, but could easily become a hassle, as plans change, people need different directions, and you need to arrange transportation. Most importantly, however, it rules out your bargaining power to get a group discount.

Hotels love groups, as they’re guaranteed blocks of filled rooms. Hotels will negotiate special rates with you, depending on availability and the number of rooms you need. These rates will almost always be cheaper than the rates you could book individually online, even on so-called “discounted” Websites.

Third-party reservation sites, like Expedia, Orbitz, and Hotels.com, offer “group booking” services to help you navigate the process. If you try to book more than nine rooms on any of these sites, you’ll be taken to a “group booking” page that asks for your contact information. A salesperson will then contact you, discuss your needs, and come back with quotes from hotels.

This is a helpful service, of course, but if you already know which hotel you’d like to stay in, we’d strongly suggest checking directly with their sales department, as well, as you’ll eliminate the middleman and most likely land a better deal. Good luck!

Have a question for us? Ask the Cheapos!