There is no way I will venture out on a trip unless I'm sure there are reservations made for each night's stay. Why? Because we tried taking a chance once and it ended up with us sleeping in the station wagon with three kids and trying to keep warm by covering up with beach towels. Take my word for it, you do not want to travel I-90 to Niagara Falls without reservations.
It was a Friday night, we left in the evening, a day earlier than our scheduled trip with the intention of finding a place along the way and arriving earlier at the Falls than planned. Between a large car show and several other events there were no rooms between Cleveland and Erie, PA. A van beat us to the last room at the Holiday Inn in Erie. We started back toward home and gave up at the state line, pulled into a rest stop and sandwiched between semis, settled in for the night. Needless to say the first day at the Falls found us struggling to keep our feet moving.
We once met a couple from the UK who were touring Australia and they had booked their first and last night of their trip but all the rest were a matter of pulling in somewhere and finding a room. I still like to know where my head will rest each night rather than chance a Niagara Falls experience.
Knowing my feelings on the matter Bob books our stays ahead of time. Sometimes he uses an online travel site but mostly he deals directly with the hotel or B&B. When you are dealing with an unfamiliar area and an unfamiliar hotel or hotel chain, you can't always count on getting the best room for the money with an online site.
The deals, you say. Well, yes there are great deals on online sites but sometimes there are hidden costs. Be sure to look for "additional fees may apply." There may be resort fees, cleaning fees, pool fees, the list goes on. By checking directly with the hotel, you can ask up front about additional fees.
It doesn't cost anything to join a loyalty program for a hotel and it can get you some extras like free WiFi, a better room, or as we found one time, an upgrade and a warm welcome with a sign and all because Bob was chosen as the customer of the day. It was fun.
Always use a credit card to book your room. It will save you a lot of trouble if you have a problem. Using cash or debit will not be so easily refunded if you find yourself in an unsolvable situation.
And be sure if you are booking an overseas trip that takes you over the international dateline that you have booked for the correct night. It's embarrassing to show up at your hotel and discover that you were a day early or late.