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Is it reasonable to assume that because you're travelling off season, occupancy rates will necessarily be lower thus saving the need to reserve accommodation ahead of time?

What I'm trying to do is allow greater travel flexibility, I'd like to be able to decide where and how long I'm staying when I'm there. Booking ahead of time will guarantee you a spot at the cost of fixing your travel dates but I'm willing to take some risk with pricing to gain the flexibility.

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Basically, yes. Traveling out of season you do not need to make reservations.

But if you travel in the low/closed season you might find many places closed and the few that are open very popular and at times booked out when you want to stay. And when weekdays are low season already, the weekends might still be mid or even high season. Further more, you need to be aware of long weekends and (school) holidays in the wider area from which people might come to visit your chosen location.

These days it is easy to book online, a few days before arrival, or at least check availability a few days ahead so you know to book or call ahead when you see very few options to stay where and when you want to stay.

This goes for hostels and cheaper hotels I know from experience, I guess this will also be true for more expensive hotels and for campsites and such.
Hotel booking sites are readily available and you can use several to cross check your findings.
And you can call a hotel you are considering, they might tell you whether you are needing to book ahead, or they might take a phone reservation to hold a room for you.

As indicated in one other answer, you can make reservations that have a free cancellation policy as well. This allows you to be sure of a place to stay but will allow you to change your plans. I would only make reservations when there are fewer rooms to be had and with the intent to use the room, as hotel owners would like that better. But when you are free to cancel, you are.

An other consideration might be the time of the day you arrive. If you arrive early in the day, with good chances to go to an other place if you do not find a place to sleep, you can take more risks than when you arrive late in the day or after the last train and bus out of the town has left.

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Generally yes, but you need to be aware that the local definition of "Off Season" can vary quite a bit. Most places have really busy times that you may not be aware off. Boston, for example, has "Marathon" in mid April and "College Graduation" in mid to end May where it's almost impossible to get a room and where rooms are quite expensive.

  • Quite right, but these kinds of events would be mentioned in just about any travel wiki/guide so I could theoretically plan around them – blackbird Jun 27 '15 at 15:07
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    @Blackbird57 You won't find everything on travel guides. A sport final, or a big conference in an obscure field, will bring in enough travellers to drive the prices up, if not to get hotels fully booked out. Do not expect your flexibility to come for free. – Federico Poloni Jun 27 '15 at 15:23
  • @FedericoPoloni there's definitely a tradeoff, added a note in the question about that – blackbird Jun 27 '15 at 15:33
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This doesn't directly answer the question, but it's too long for a comment. If it's out of place, feel free to delete.

As others have said, off-season rooms are usually available without a reservation (and often below normal/advertised rates, through sites like booking.com, priceline, etc). But one strategy you might consider employing is taking advantage of the free cancelation policy of many hotels, if you cancel 24-48 hours in advance.

First, many hotels extend their free cancellation policy to the duration of your stay, meaning that you can cancel mid-reservation, as long as you give notice 24-48 hours before you intend to vacate the room.

Example: With a reservation from July 1 - July 8, you can inform the hotel on July 3 that you intend to leave July 5, and you won't be charged for July 5-8. Of course, this varies by hotel (and perhaps by booking site), so read the fine print before counting on this strategy!

For hotels that don't allow mid-reservation cancellations, you can make two separate reservations, as long as the second has a free cancellation policy.

  1. Make a reservation for July 1-4 at Hotel A.
  2. Make a second reservation for July 5-8 at Hotel B.
  3. If you decide not to stay in the city, simply cancel your reservation at Hotel B on or before July 3.

This doesn't provide perfect flexibility, but it provides some.

Using either strategy, you may also have the option to look for a cheaper/nicer/cooler/hipper/better hotel after arriving in the city, and change hotels after you've arrived (even if you do stay in the city).

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"Trust but verify."

If you're traveling during a "real" off season, occupancy rates will be lower than usual. But there may be something peculiar to that location (a conference, sports event, etc.) that nullifies this.

The "safe" way to play this game is to monitor the hotel vacancy rates for your target dates over the internet in advance. If somehow, rooms are filling up fast for your dates, you need to make a quick decision about what to do.

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