Lake District August 31-September 6

What website are you using to look at trains? I am curious why it did not show a route via Glasgow. We use National Rail to find routes, fares and tickets throughout the UK.

https://www.nationalrail.co.uk/

You will see that the route from Oban goes Oban—-Glasgow Queen Street, then Glasgow Central to Oxenholme to Windermere. So you change stations in Glasgow but we have walked between the two with no trouble.

Trains from Oban go to Glasgow Queen St, not Edinburgh. You then want a train from Glasgow Central south to Oxenholme, where you change for the shore branch line to Windermere. The two stations are. maximum of 10 minutes walk apart. there is also a bus service between the two but given frequency it is usually quicker to walk unless you have mobility issues. There is absolute no need for a private driver, which will cost a fortune and is unlikely to be any quicker. For example you could get a train from Oban at 8.57 which would arrive in Windermere at 14.56.
From Windermere there are trains direct to Manchester Airport every two hours and in between there are other options with a simple change at Oxenholme. For example there is an 18.56 direct service on weekdays. I checked a random date in May and you could buy a ticket for £9pp for that train.
Assuming that you travelling by train from Manchester up to Oban and back via Windermere you can probably save by buying a railcard. If it is the two of you a TwoTogether card for £30 would give you 1/3rd off all fares. The only catch is that you can't use the railcard before 9.30, so you would need a later train from Oban in that example above - there are later options.
You won't be able to buy tickets yet - usually around 3 months ahead of your date. Try and avoid travelling at weekends if you can as there can often be engineering works which will mess with your plans.

You would have to change train at Glasgow to get to Edinburgh, and trains from Glasgow to Oxenholme for Windermere tend to be cheaper than ones from Edinburgh, especially at that time of year.
If you don't want to walk Queen Street to Central there is a station link bus. #398- free to rail ticket holders. IMO it takes longer than walking, but it is there.
GLA/EDI to Windermere you change trains at Oxenholme.

Mountain Goat are far and away the best in the business in the Lake District.

Windermere to MAN airport take a through train at 0955, 1307, 1600 or 1856- rather than one where you change en route.

Windermere and Bowness have hundreds of places to stay. Are you looking at hotels, B and B's, self catering flats/cottages?

Cheap train tickets to Windermere open exactly 8 weeks (2 months) before travel, not three.

Thank you so much. We have been to York and Edinburgh on a previous trip, so wanting to do the west coast this time.
We will be traveling to Glasgow before coming to Lake District. Not sure yet if we will fly into Manchester or Glasgow - depends on pricing and timing. I am looking at a tour of Skye and then want to spend two nights on Iona before coming to Lake District which will cut our Lake District tours to 2 days.
So train wise, we may take a train from Manchester airport to Glasgow - maybe not if we fly into Glasgow.
We will take a train from Glasgow to Oban.
We will take a train from Oban to Windermere.
We will need to take a train from Windermere to Manchester airport (thinking easier than back to Glasgow).
I have enjoyed the B&Bs in England on our previous trip, so that would be my first choice. So you think we can make it from Windermere to Manchester airport for a 1:45 flight on the same day, or do we need to spend a night in Manchester before our flight home?
Thoughts?

You can definitely get to MAN in time for your flight but personally I don't like being a long way from an airport on the day of flight, especially for a long haul flight. You could go the night before and stay in central Manchester and enjoy a night there before a short train to the airport the next day. Or catch a late train from Windermere, which would allow you time for another day tour, before taking a train to the airport in the evening.
In truth going back to Glasgow is not especially difficult either and would be worth doing if you see a decent flight cost just using GLA. Although in truth there are probably more choices into MAN and it does have the advantage of a railway station at the airport. For GLA you need to take a bus or taxi into and out of the city.
One of the options from Oban to Windermere suggested a change at Dalmuir to catch a train into Glasgow Central, this avoiding the walk between stations. That option had an hour to wait at Central - OK as it's right in the city centre and plenty of places for refreshments. But also about 50 minutes at Oxenholme, which would be less attractive. But you could just get a cab from there to Windermere from there.

A true story from last Saturday. The 0613 Edinburgh to Manchester Airport (the train you would use from Windermere via Oxenholme for a 1345 flight from MAN) was platformed at Edinburgh for an on time departure. Just as it was meant to leave there was a major points failure just outside Waverley.
That took just over 90 minutes to clear.
The train had then lost it's path, and finally arrived at Preston 113 minutes late, where it was terminated short, passengers being transferred to the two hours later service running 7 minutes behind him- leading to a chock full train.
The next train out of Edinburgh for Preston, the 0652 was held behind him, but overtook him at Carlisle.
The next two trains south were cancelled (advertised cancellations due to no train crew).

How do I know?- I was meant to be on the 0613, joining at Carlisle. I got the only other train running at 0746 to Lancaster (for Euston), had a meeting there and was back at Lancaster station when the 0613 finally arrived, and I then joined the 0812 from Edinburgh to Manchester Pic.
That 0746 was a short formed train, packed with hen parties and football fans, and was standing room only.

So last Saturday you would have missed your flight.

And yesterday, again at Preston, I had a heavily delayed connection due to a signal failure a long way south. I had an important meeting to get back to in my home town, so ended up having to catch an earlier train. Fortunately I was tracking both my inbound train and my connection, and ended up making a 60 second connection from platform 3c to a train at the far north end of Platform 3 (which couldn't have been further north on 3 if he'd tried). I leapt in through the back door (first class door) just as the guard was about to close the door. If I had had to even momentarily pause I would have missed him, and been 70 minutes late getting home. There wasn't even time to shout down the platform to the train dispatcher to hold for me.
Before that I had had an earlier cancellation at Blackburn due to lack of train crew. Not my day.

These things just happen.

Will respond to your PM shorty.

Do pay attention to the above cautions about timing your train back to the airport, and stay close by.

We have had train delays in the UK due to all kinds of reasons, from signal failures to staffing issues to a suicide on the tracks that required investigation.

Co-incidentally I was on a train that came into 3C today, for the first time in years. It is a long way to anywhere else on the station, although I suppose an 11 coach Avanti train would have been quite close. No drama though, it was on time and I was cycling home.