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歌ってみた (Utattemita) roughly translates to "tried to sing". It is a subcategory of the yattemita section on nico, where users upload videos of themselves trying various things like dancing, drawing, and singing in this case. In the utattemita subcategory, users upload videos of themselves covering various songs. Generally the video doesn't actually show the person singing the song; instead the cover is played over the original PV of the song most of the time.
In the past, most uploads in the utattemita subcategory were of anime songs. Nowadays, they are almost entirely Vocaloid covers.
First off, get a Nicovideo account. There are a lot of English language tutorials out there in assisting with signing up for an account which can be found easily by googling, but I think Nikki's guide is the most complete.
Once you have an account, you can access the utattemita subcategory by first clicking on ランキング (Ranking) near the top right corner of any nico page. This will bring you up to the ranking page, which shows the daily 20 top videos of the major 6 categories on Nico. Then click on the やってみた (Yattemita) category, and finally click on 歌ってみた. This will give you the daily top100 videos in the utattemita subcategory.
These videos are basically community only uploads. To view them, you need to first determine who uploaded the video, and afterwards go ahead and join their Nico community. This should allow you to watch the video.
There's a wide variety of programs that can do this task. Googling can give you a couple of results. The best tool is probably Nicoplayer, a Japanese program that can not only download the nico vids, but the comments as well. The Mozilla Firefox add-on Nicofox is also quite good.