Even when it's warm or hot in summer, I don't think we ever hear of the CS girls sleeping outside at night! As opposed to lessons/resting outside during the day, which Miss Bubb hates. But, especially in Austria/Switzerland where summers probably tend to be more reliably warm than in Britain, could you imagine them doing it at night? In at least two of the three books I've got about the history of a specific girls' boarding school, it is mentioned that they once used to do just that in hot summers (in southern England), before security was such a big concern. On the roof of a boarding house, or the grass. The girls would beg to do it. In one of the books, I also read about something called "long rest" outdoors in the day (on Sundays I think), seems rather CS-like. Quite often when reading these books, I nod and think something explains whatever thing in the CS puzzled me.

We certainly did not sleep outside at boarding school, in Scotland summer nights would probably often have been too cold anyway. I believe all or nearly all schools are nowadays closely monitored by CCTV throughout, have several other security measures. Think my primary school (in suburban London) has an intercom at the gate, sure it didn't when I was there. Being so remote at boarding school, there was generally little need for any security at all.

Not sure the front door of the main building was even locked at night, think most boys' boarding house doors including mine, were left open. Quite possibly the girls were locked in, but they could probably easily have got out of a downstairs window, and unauthorised night wandering was pretty common for girls and boys IIRC. The staff maybe often tolerated it within reason. After I left, they apparently tightened up a lot. Even on their very last night, the upper sixth were kept firmly indoors, unlike with my year.
Back in the 80s, we once drove up to my mothers' old boarding school, which is near a city in northern England, in the holidays, parked, walked around, and took a photo or two. Not sure you could do that now without being stopped.

If the CS had survived to the present day, it would (sadly) presumably have become far more security-conscious, both in Switzerland and/or Wales. I'm sure someone wrote a drabble once that mentioned the Swiss school regrettably being far less open than it used to be. As for them sleeping outside at night, I don't know. Would Matey have allowed it? She doesn't generally seem like the type to give in to begging at all. This is stuffing too much into one thread really, but presumably their summer bedding was a lot thinner than in winter. And by the way (unrelated), isn't there something about girls not being supposed to read in bed whilst lying sideways? What on earth was the issue with that?

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Sleeping outside: At the beginning of Camp, Jem tells Grizel, Juliet, Joey and Elizaveta to sleep out because the weather is so hot but I can't think of any example of this happening at the school itself.
In New House and, I think, Wrong, there's examples of people sitting outside in deckcjhairs and "lying around" because of the heat with lessons being cancelled, and, as you say, there are rest periods and lessons outside.
Whether there would have been sleeping out at schoo in Austria seems to me to be unlikely. There's a number of mentions of closing the jalousies (blinds) and opening windows to keep dormitories cool. I can see Matey going down the road of "why sleep outside with the potential for playing about and disrupted sleep if the dormitories are cool?". The CS books are rather hot on getting a good night's uniterrupted sleep. We hear of but don't see, weekend camps during the summer term(s) and I suspect that's the closest they got to sleeping out.

Reading in bed: The girls were supposed to read sitting up and wearing a bedjacket. It was thought that reading lying down was "bad for the eyes" and, it surprised me to find out, this is true. Reading lying down can cause eye strain. Also it's bad for your neck and back.

Security: There are several episodes of girls getting out at night:the late night skating where Dr Russell reappears, the Baby Voodoo incident, the snails incident, Grizel, Eustacia, Gay and Annis running away, the pigs in the meadow... so the school can never have been particularly secure at night. There's even a burglary in Goes To It.
Realistically, the area of H&S has seen great changes over the years and it's not hard to find incidents in the books which would be unacceptable now.

Everything's more secure now. I remember, as a kid in the early 80s, everyone at our class in primary school solemnly planning to get out of the house and go off on adventures like people in Enid Blyton books did ... and then wondering how we'd manage it without setting the burglar alarms off and finding the keys to unlock the front door!

Even day schools are more secure now. I had a meeting near my old school and thought I'd drive up to the place for a quick look - just outside, I mean -, only to find that I couldn't get past a gate. In my day, not only could you get right up to the building, but the doors were open so anyone could wander in and out. The door by the lockers, used by pupils, wasn't even shut, never mind locked.

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Thinking about it, a lot of modern security is electronically based - burglar alarms, surveillance cameras, motion detectors and automatic lights, locks that automatically open in the case of fire or other emergency. You can easily lock a building so no-one gets out at night, but that can lead to horrific death tolls in the care of a fire or other disaster. With early CS era tech, to be secure, they'd need a wall (probably topped with barbed wire), with a couple of exits, and a night watchman to keep an eye on things. What they had was multiple buildings, the first couple converted from hotels or houses, a thing for fresh air which meant that windows were open at night, and a privacy fence. Physically, it would be quite easy for a student to leave; the main defence would be the shared dormitories (being able to get up, get dressed and leave without waking your roommates) and convincing the girls that this was a bad idea (say, via automatic expulsion for leaving the property in the middle of the night).

As far as sleeping outside - I'm not familiar with Austrian alpine weather, but waking up at dawn covered in dew isn't pleasant, and neither would having to wake the girls at midnight so they could go inside before a thunderstorm hit.

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My last school - I went to 7 - had about 5 different doors to get in and out when I was a pupil there. A local voluntary organisation had a room in the basement which you could access from one of the side doors. Later, the whole building, including the basement room, could only be visited if you signed in at the school office (accessed from the front door), and later still I discovered that I was only allowed in because the secretary recognised my name. A respectable 80 year old retired engineer trying to get access to the basement room was refused access because he was a man. He was undertaking research on behalf of the community but apparently that made no difference. No member of staff could be summoned to escort anyone through the school (just in case they encountered one of the girls) so no visitors were permitted. Shortly after, the organisation upped sticks and moved to a building that allowed access for both men and women. The local primary school has an entry phone but if you can pass that test they don’t seem to care who you are.

Some of the larger local houses were built with sleeping porches (balconies) overlooking Hampstead Heath. Sadly many of them have been altered in recent years to create an extra room.

I was going to say I couldn’t imagine my boarding school allowing us to sleep outside, but then I remembered the horrid camping weekend on the lacrosse pitches. It was 5 minutes from the school building and of course it rained.

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I think some schools here participate in the "sleep out" charity event, to raise awareness of and funds for homelessness. But aside from that, we definitely don't have the weather for it to be a thing!

My school took us on a trip to Italy, and the girls I shared a room with decided to sleep out on the balcony one night. They reckoned without the teachers doing the last-thing-at-night rounds, and the PANIC. They found the blankets & pillows on the balcony and panicked - why were they there, could we explain it? And they couldn't immediately see me, because I was drying my hair where the mirror was, out of sight of the door. Where was I?!

They very bemusedly pointed out that I was only a couple of feet away and didn't need to be shrieked for, and brought everything back inside.

Of course, I have a bit more sympathy now with a couple of teachers bringing a load of teenagers out of the country on a trip