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My Daughter has just turned 3 so have had a good amount of experience with this over past couple years.
My tried and tested method is to book a points redemption and then email hotel and casually ask for a cheeky upgrade (while slipping in that I’m Diamond Ambassador) to a room that would have a little more space for a travel cot (now an inflatable bed thing) and from there you can see how the hotel wants to play it. Sometimes they say no probs or sometimes they say they can upgrade for a fee (which is then a lottery, as to if they remember to charge you or not when checking in/out).
We’ve never really had an issue and quite often, if they know you’re arriving with a baby/toddler, hotels are usually pretty good at accommodating that and maybe give a branded teddy or similar – which always gets a smile.
If I’ve ever agreed a fee, I’ve never paid up front. Firstly, they may forget to charge you for the upgrade. Secondly, a cashback deal you can use may appear on your amex before the stay. And thirdly and most importantly, you can usually cancel a points stay up to the day before without penalty, which can be very useful when your kid is suddenly taken ill and you’re in A&E when you’re meant to be packing and have to cancel the trip.
P.s. only stayed in the Glasgow Kimpton once. We arrived during a fire alarm with all staff and guests out on the road. Once back in (only 5 mins later) they upgraded us to a lovely suite and gave us high-tea for the [minimal] inconvenience, so may be worth wafting a candle beneath a smoke alarm when first arrive 🙂
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