Switching from paper to digital booking, advice/tips?

So my family has built and owned an inn for 22 years (bigger than B&B, but still smaller hotel, approx 20 rooms). Currently all reservations and records are kept on paper. Their "online booking" is sending an email through their website. I keep telling my parents (owners) that if they switch to a booking software their life would become easier. They also are considering getting integrated with booking website (travelocity, etc) to help fill rooms as they have had a hard time getting booked some of the slower winter months. I've tried researching different softwares by just googling them, and I'm having a hard time finding the info I want. Can anyone help give me some direction in companies to look into? The owners need something that is very user friendly because they aren't always the best with computers. The software also needs to be somewhat affordable...but I'm not even sure what the price ranges are for these softwares. So any info would be very helpful!!!! I want to help their business, but I'm at a loss of where to start.

First of all, regardless of getting on other websites.... get off the paper. It's too cumbersome. Something as simple as Beds24 or ReservationKey. It will keep track of the rooms and everything else. Should be a whole $30 a month or so. If you want to hook into OTAs, both have options for that... MyAllocator for ReservationKey and they have their own channel manager for Beds24.
Most of the other software is expensive. Cloudbeds, which runs my allocator doesn't seem to understand how taxes work (which drives me CRAZY) would be $190+ a month, for example and still thinks we all live in a VAT society with singular rates.

Look at ReservationKey.com. They have a sliding scale of fee (# of rooms) and a lot of features useful for housekeeping (stayover/checkout), record keeping (taxes), etc.
They have a 30-day free trial. Feel free to make a reservation for my Gillum House B & B for Nov 10 - I am on their website as an example. It will be a real-time reservation. I do not take cc# online although most do. You need not worry about messing me up by making that reservation because it is a day that I block out for B & Bs for Vets (Nov 9-11).

There are lots of discussions here alread on the topic just do a search and you will get info. I can't tell if you the number of people I have convinced to do this over the years. Am working with a client now. We are using Reservation Key. Many folks here use it as well. It will do most everything you need. Google them and get 30 day free trial

Hello and welcome! You are right where we were about 2 years ago. (I sent you a private message on how we did it.) We didn't even take credit cards so it was a huge learning curve for us. Now we have an online booking website, charge credit cards through Square, and business is thriving. To top it all off, we are enjoying life here at our inn! That's the important thing!

Folks here suggested Reservation Key and encouraged me to go online about a year ago, it has been great and nothing stops you from running both systems until you become comfortable with the idea. I'm in the old folks category, but comfortable with computers, the wife not so much. It is faster for me to write information on paper and then transfer to the computer and for now the old paper book serves that purpose, for the many reservations that arrive by the online system I print them out and pass on to the wife so she can write in the book. Yes it is redundant, but it lets us ease into the future at our pace. We pair this system with Authorize.net and run a small deposit when reservations are made, I think it cuts down on the folks who just want to tie up a room "in case" they want to visit and the few cancellation fees (lost deposits) go a long way to paying for the use of the online system.