I've been an amateur astronomer for more years than I can count, and I've helped many people choose their first telescope.
However, I usually recommend that most people start with a very good pair of binoculars instead of a telescope. High-end binoculars are wonderful instruments that will remain useful even if you decided to upgrade to a telescope. I still use mine regularly despite owning multiple high-quality telescopes. They're just fun and easy.
- $100-$150
The Celestron Skymaster 20x80, which you can find for a little more than $100 online, are great for viewing large nebula and star clusters like Messier 42, Messier 31, and Messier 13. In extremely dark skys you can even see Messier 81/82.
The downside is that they are heavy and big for binoculars, which makes them a bad choice for little kids. But you can supplement them with a tripod, which is even nice for adults who want keep them very steady when observing faint or small objects.
As an alternative, consider the Orion 20x80 binoculars.
If you'd rather have something you don't need to hold up with your arms, or you want something that a small child can use, then a table-top telescope is the next step up.
- $100-$200
The Orion Skyscanner 100mm will give you similar viewing as the 20x80 binoculars, but with a mount that is more friendly to those who have weak arms or difficulty craning their necks to look high in the sky.
As an alternative, consider the AWB OneSky 130mm Reflector, which is recommended by Wirecutter.
The next level up requires a bit more commitment. It's more expensive, but also less portable.
- $300-$400
The Sky-Watcher 8-inch Traditional DOB is a Dobsonian telescope, which means it moves around like a cannon. It's very easy to use, and this is the same kind of mount used by the most expensive amatuer telescopes.
An 8-inch aperature will allow you to see all the same wonderful objects as the previous options, but you'll also get good views of Jupiter, Saturn, Venus, and some fainter objects like Messier 27 or even comets (when they're around).
As an alternative consider the Orion SkyQuest XT8 Classic Dobsonian.
- $600-$700
I don't usually recommend a GOTO or tracking telescope for beginners. They are finicky and can be difficult to get started with. I also think a GOTO system takes some of the joy out of learning the night sky.
But if a GOTO is what you want for your first telescope, I recommend the Celestron NexStar 5SE. Once it's calibrated, you can use the hand controller to automatically slew the scope to almost any object in the sky.
Don't assume that these are for the lazy--they're often more of a pain than a dobsonian. However, Celestron has really made some quality GOTO instruments, and that's why I recommend this one.
I also recommend picking up a copy of Turn Left at Orion to help get you started, no matter which scope you choose.