Hi M.,
I can't speak to the hotel issue, as we've always had the option of staying with family. I do, however, usually end up putting my daughter in bed with me at least part of the time when we travel for her sense of security. Also, ask yourself how much time will actually be spent in the hotel vs. visiting with friends and family in the area.
As for traveling alone...It is possible. I traveled alone with my daughter at 19 months and with her and my husband at 23 months. Both times she rode in my lap. Some advice:
Pack lightly and smartly for the plane. You'll have to manage everything you carry on the plane and your son through security and the airports without assistance. I go for ONE carry-on bag that will fit under the seat in front of me. I can't carry more than that easily, and I can't get to one in the overhead bin without asking someone for help anyway. Organize your bag with gallon zip bags. Snacks go in one. Toys in another. Diaper supplies in a third...etc. It will help you find what you need without going crazy, especially one handed. Have everything you need to pull out for security (ID, baggie of liquids (including trial-size baby Tylenol), boarding pass) right on top.
Go to the used book store and stock up on Little Golden Books. They're about $.50 at ours. Depending on the selection, you'll find classics and ones with Sesame Street/Disney characters. They're light and smaller than most books, and many have just the right amount of text to keep you busy without getting bored.
Go to the dollar bins at Target, the dollar store or the party store and buy little party favors, a coloring book and new crayons. Don't let your son play with them until the flight so they'll be new and exciting. Plus, you're not making a big investment in something that may end up lost en route. I've even heard of parents wrapping them like gifts to add to the fun. Also, hide a few favorite toys about a week before the trip. He'll be so excited to see them again, that he'll play with them for a while.
If your son is fairly active, invest in a backpack with a leash for him. A friend uses one (looks like a stuffed monkey... http://www.walmart.com/ip/Goldbug-2-in-1-Monkey-Child-Saf... ) for her son, and loves it. He can run some of his energy out at the airport while her hands are occupied with the carry-on bags and the stroller.
Use overnight diapers for travel days. You won't have to worry about changing him on the plane as much. That can be a pain, as plane restrooms may not have changing stations, especially on smaller planes.
I always buy some bottled drinks for us in the airport and pack an empty sippy cup. I fill my daughter's cup during boarding so she has the option of drinking if her ears bother her during take off (never the case, though) without waiting for drink service. The added bonus? I have a drink for myself with a LID. I don't take an open cup from flight staff unless she's asleep.
Pack snacks. Applesauce or fruit cups should go in a quart-zip-bag and come out for security. Get disposable bibs, adhesive placemats (for eating or play-doh) for the tray table and silverware to stash in your bag.
Use the umbrella stroller in the airport and check the car seat. If you use a car seat travel bag (http://www.walmart.com/ip/JL-Childress-Ultimate-Padded-Ca... ...I hang my carry-on on the stroller, wear the carseat and pull the suitcase), there is room to pack a package of diapers in the space where baby sits in the seat.
And lastly...Mentally plan your sequence for security. (And wear slip-on shoes.) I do: 1) Shoes off of my daughter while in line. 2) When next in line, daughter out of stroller and in arms. 3) ID and baggie out. 4) Stroller on conveyor belt. 5) Bin on belt. Daughter's shoes in bin. 6) Bag on belt. 7) My shoes and baggie in bin. 8) Push everything through. Look for family-friendly security lines (SEA-TAC is great about this). And other travelers frequently offer to help me with my stroller.
Best wishes!