Q: Is there any obligation to sleep in a Sukkah? Answer: The question is asked in Halacha regarding the obligation of sleeping in the Succah on the 7 days of Succot. Maran, in siman 639 clearly writes that the obligation of sleeping in the Succah is even more stringent than the obligation of eating in a Succah. When it comes to eating, the obligation only applies to certain measurements of food. But when it comes to sleep, short naps, dozing off, and even what is called ‘Shinat Arai’ (temporary sleep), all are forbidden outside the Succah.
The Mishna Berura gives an explanation for this. The Mishna Berura says that a short nap or temporary sleep can satisfy one’s need for rest. When it comes to sleep, if a person takes a nap for just five minutes, he can become refreshed. On the other hand, a certain amount of food would be needed to satiate one’s hunger. So when it comes to sleep, even for the shortest duration would be required in the Succah, but when it comes to food, a measurement applies, and thus sleep carries a stronger stringency
So now we discuss a question with regard to sleeping while traveling. Is it permissible on Succot for a traveler to sleep while in transit? Would it be permissible for someone to sleep while he is on a train from Brooklyn to Manhattan, or while traveling as a passenger in a car, or while in flight to another city? So the answer is that it depends on the type of travel. You see, the Gemara says that travelers are exempt from Succah. But that applies only to a person who is traveling outside the city and is not coming right back like when traveling on a plane. But if a person is just traveling on a train and he is going to the city and coming right back, then that doesn’t qualify him of having the status of a traveler. So he would have to be careful not to fall asleep on the train.
But there is a very interesting observation that is brought down by Rabbi Elazar Moshe Halevi Urvitz who was the Av Bet Din of the city of Pinsk. He made his observation on the Gemara Succah Daf 26. He said that the Chachamim did not make a decree that one is not allowed to fall asleep outside the Succah. The Rabbis did not decree that you can’t sit outside the Succah and suspect that you might fall asleep. The issue is that one should not sleep on purpose when outside the Succah. That is a problem. But falling asleep accidentally is OK.
So if a person is on a train, and he dozes off unwittingly, then that is OK. He would not be in such a case transgressing the restriction of sleeping outside the Succah. Sleeping outside the Succah is only forbidden, according to the Rabbi, where he does it with intent. If one puts his head down for 5 minutes and falls asleep, then it is a problem. But, if sleep came over him without intent, then he is not transgressing.
So, Halacha Lema'ase, one should try to sleep as often as he can in the Succah. One should move his cot or bed into the Succah and make every effort, especially when the weather warrants, to sleep in the Succah and fulfill the Mitzvah as it was meant to be.
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Hachamim 
