Perhaps you’re a couple planning a destination wedding and you need to book a block of rooms at a hotel for 40 guests? Or, maybe you’ve been tasked with finding hotel rooms for your kid’s soccer team? It sounds simple at first; to book a room block for your group at your hotel of choice on your favorite online travel site. But, as any professional event planner will tell you, it can be a lot more complicated.

Here’s why…

First, on most of the popular online booking sites, like Expedia, Kayak or Travelocity, you enter your trip details, like destination and dates, and then start your search. Most travel websites default to searching for only one room at a time; which can doesn’t help you find hotels with availability for your entire group. The next roadblock: the booking websites only allow you to reserve eight rooms per booking. Depending upon the size of your group, that means that you would have to book multiple reservations to accommodate your entire group, and that’s a huge headache to manage.

Instead, you could decide to simply call hotel after hotel directly to ask them about the possibility of booking a room block for your entire party. Your call would be routed to the sales department at each hotel and, if there was inventory available, they would be happy to name a price and send you a contract. But, booking a room block directly, as a non-professional planner, is not as simple or risk-free as it may seem.  Sometimes the lowest quoted rate may not be the best value for your group, there could be additional daily Resort Fees or other user fees that can really add up.

Also, don’t assume the rate quoted to you is the best available and make sure you know what’s included. There’s no harm in requesting a lower rate or upgrades and extra concessions. Most people don’t know the extensive list of available discounts and upgrades available to groups just for the asking, like free WIFI, suite upgrades, complimentary rooms and reduced parking fees, to name a few.

Also, when you book a group of rooms, the hotel will require you sign a legal contract, with some significant performance requirements. Failure to read or understand your obligations under that contract can lead to serious financial penalties. For example, if you book 40 rooms and only 30 people show up, you may still be obligated to pay for unused rooms, unless you’ve negotiated an attrition allowance. Hotel contracts can have pretty restrictive cancellation policies, too, leaving you on the hook if you event cancels or changes.