How do I find the cheapest date to book a given hotel?

For the hotel chains Hilton and IHG this is possible:

Hilton

For Hilton this is an official feat of their booking site. Select a hotel, a room type and a rate, click "change dates" and you'll arrive here:

check the button "Use flexible dates" and you can see the best rate and scroll back and forth by as much as you want.

tip of the hat to travel-dealz

IHG

For booking hotels of the IHG group (Intercontinental, Holiday Inn, Crowne Plaza, ...) you need a workaround similar to the one for Hostelworld in my other answer.

Again go to the booking site, choose a wide range of dates, a hotel, then a room type and then your rate. Proceed to the next booking step and there on the left under "Your rate" click "View Rate Description and Rate Rules" where you find the rate per night:

This is less convenient than for Hilton as you need to span a wide range of dates first and then check again for the dates that you find to be cheap. Also make sure the rate you wish to book is available throughout the whole range of dates you are looking at. E.g. for IHG the cheaper non-flexible rates are typically only available until 3 days before booking.

Hostelworld has a price breakdown that we can use with a few drawbacks.

If you can find the hotel/hostel/spot under the bridge that you want to go to on the website, you can specify a travel period ("stay") of up to 15 days. Then pick your place and go to where the price is displayed. You will find the option "View price breakdown" give you the price per night:

For this property in NYC in Sunday and Monday nights seem to be cheapest in April 2016.

The method is not perfect, here are the catches:

1. You have to find the place you are looking for on the site. Hostelworld does have a decent selection of hotels, but you will not find a Grand Hyatt, apologies.
2. If you are looking at prices over long periods, you have to do a ton of searches due to the max 15 days stay limit.
3. Your desired hotel/room type may not be available on one of the days in the 15 days and not be displayed.
4. Some hotels may have a shorter maximum stay and not enter that list (even though I found them displayed).
5. A different rate may apply for your actual duration of stay than for the 15 days search period and the hotel might have a minimum duration of stay.

You'll have difficulties to find such a site. Still, a bit of logic will allow you to predict which dates are the best and then you'll just need to verify that your assumptions are right.

Here are the factors influencing the hotel rates/level of frequentation:

• school holidays
• major convention or event in the city
• bank holidays next to a week end
• best weather period

So the lowest rate would be during worse weather period, outside of school and bank holidays period during a week where there is no major event in the city.

Usually Sunday evening is the night with the lowest price.

Sites like Kayak are allowing to set alerts that will email you every day the pricing for a flight or a hotel.

So, a bit of digging shows that this isn't a new question.

It's been asked in several places around the Internet.

One notable example is a site called MightyTravels, which, in an article about this exact problem, makes an interesting claim at the bottom:

Did you know – with Mighty Travels Premium you can search 365 days of hotel rates sorted by deal price or savings off the average rate. We cover 20,000 different properties.

However, their page about their premium service makes no reference to this feature. Therefore the above quote seems likely to either be a lie, or a now discontinued feature.

I can find various persons claiming that Kayak does (or at least used to) offer this functionality. However I cannot find it now. TripAdvisor SuperSearch's google description claims it offers this, but again, no sign of it on the actual site.

I have however found two actual, meta-search possibilities:

• Hotels Combined - there is a check box on the search page saying "I don't have specific dates yet". When you perform a search like this, it seems to work, providing a list of hotels with their cheapest 1-night rates. However, clicking through to find the actual dates they are offered, instead shows you the prices for the last dates you searched with (or the default dates if you didn't)
• Booking.com doesn't explicitly provide this, but it does (sometimes?) try to help you out, by suggesting other dates with cheaper available rates. The box sometimes pops up in the sidebar, sometimes at the top and looks like this:

Finally, in addition to the IHG and Hilton options offered above, the Marriott chain offers probably the best option of the lot. Go to their site, enter a location (approximately), click the dates box, then hit flexible dates when the box comes up. Enter the number of days (doesn't seem to offer flexibility there), then pick an individual hotel. You know get a month-long view of prices for stays beginning on every date, and can easily step backward or forward a month.

There's an easy way to do this for a limited set of cases. If your destination is a popular tourist area, go down to a bricks and mortar travel agent and get a brochure for holidays in the area. Most of those have a table of prices for the same vacation on different weeks or months. From that you can tell which are the cheap months.

If you don't want to do that you can approximate the same thing with a website by putting in a stay you might be interested in for some week, then moving the dates forward four weeks, then another four weeks and so on. Make sure you don't hit popular holiday dates.

This works because prices don't change much from week to week. February may be cheaper than May, but second week of February won't be a lot different from third week of February. Also when you find the cheapest month for some hotel, other nearby hotels are probably cheapest in the same month.

For popular destinations a travel agent probably knows this information.