That is def cherry eye. It isnt bad yet, which is a good thing!!! But it probably wont stay that way. they can get irritated easily which will make them swell and in some cases (like Bacons) get infected, which makes it a very costly, time consuming, frustrating condition. Both of Bacons eyes have had cherry eye and he had to have 2 surgeries on each eye in order to fix them.
I highly recommend not trying to put the cherry eye back in place, it can cause pain and more injury if you do it wrong, plus it can cause more swelling. I have done a lot of research on this topic, and have dealt with it personally.
I recommend keeping a very close eye on it and taking him to the vet when possible, they will probably give you an anti-inflammatory salve or drops for the eye. The most important thing is keeping the swelling down, and keeping infection out. If you get Winslow to the vet before it gets big and swollen they can probably tack it down without surgery.
Cherry eye can cause blindness if it gets out of control. I didnt know this until the second vet we took bacon to informed us that the "cherry" rubs on the cornea it causes pigment to build up and that causes blindness over time. I believe this happens fairly quickly because our vet insisted we get his eye fixed sooner rather then later.
If you have any questions I can probably answer them, or if you want to know what we have been through with Bacon I have pictures and can tell you more about it.
Keep us posted, i know that it can be hard to keep up with it. Cherry eye can become very stressful and frustrating, especially when it gets to the point ours did, so if there is anything i can stress to you its get it looked at sooner rather then later when it gets worse.