How to Money · Friday, September 25, 2026
The traditional benefits of traveling during 'shoulder season' (between peak summer and holidays) appear to be diminishing. While historically offering around 20% savings, factors like increased demand and specialized deal-finding services may be reducing these opportunities.
“Okay, so let's talk about travel for just a second and shoulder season in particular. That is something that people always assume and it has been very true in the past. that shoulder season is a great time to travel. That being where we live in the United States, oftentimes it's like, we'll go after the kids are back in school because far fewer people can travel then. And so, yeah, travel in mid-September to before the holidays and you can travel more cheaply. Well, it seems like shoulder season is shrinking, Matt, according to new statistics. And yeah, If you book in shoulder season, typically the estimates are that you're going to save on average something like 20% versus if you travel during the peak of summer or during the holidays.”
“But given the technology and all the different sites and the apps and the services that you pay for, the the folks who are constantly reshopping and they only get paid if they save you money, not to mention some of the apps and folks out there who are taking even a subscription. There are a lot of different websites and software providers who are specializing in this, right? And so I think there's just less opportunity for regular folks to find a deal on shoulder season. It's like it almost requires you to participate in this sort of commoditization of shoulder season or finding a deal. Yeah.”