Windsor or London?

I think Windsor would be more restful and less hassle after a long flight. I love Windsor. In addition to taxi you might investigate a car service from LHR to your hotel. Last time I stayed in Windsor I used Windsor Cars to get to my b & b and was very satisfied. Another option to consider is the AirLine bus that goes directly from the Heathrow Central Bus Station to Oxford. I took that on my last trip to England and it was comfortable and (for me) cheaper than the train.

If you arrive at 8:40 pm, it will be closer to 9:30 by the time you get out of the airport, and that much later by the time you arrive anywhere. And you will be jet lagged. If its me, I would stay at any of the many hotels around Heathrow, and start my day fresh the next morning.

We stayed at the Ibis Styles Heathrow (5 min taxi or bus from Heathrow) and can recommend it.

As for London vs Windsor, I would always go to London, but that's just me. Taxi or bus back to Heathrow, or to Hayes and Harlington (depending on your hotel), and take Elizabeth Line into London. Plus from London its an easier direct train route to Oxford, rather than phaffing about getting from Windsor to Slough, Maidenhead or Reading to get a train to Oxford.

I would go with plan Windsor and enjoy the next morning in Windsor before moving on to Oxford. Mostly because I really love Windsor. We stayed near Paddington for one night once with our kids on our return from Paris and were heading back to LHR airport the next day. It was clearaly a train station part of town, commercial; that famous royal Mary's Hospital nearby. Not charming with shops and restaurants.

I'd have jumped on the stay at the airport that late at night. There is the Hilton Garden at T2, but I would take the free train to T4 and stay at the Crowne Plaza (my fav) or Holiday Inn Express, Premier Inn or Hilton.

Windsor for sure,

Thanks everyone for your input. For those of you who suggested finding a hotel near the airport, are there any hotels within walking distance other than the Hilton Garden Inn in T2? I would love to stay there but they don't have rooms to accommodate 4 people. I've read mixed reviews on the Hoppa Bus.

Windsor! The Macdonald Windsor hotel is great!

The hotels out on the Bath Road are also served by very frequent London bus routes, several of which run 24/7. Apart from its price, the other dis benefit of the Hoppa bus is that it serves several hotels on each route, so can take a long time to get you to your hotel. The benefit is it takes you to the front door of your hotel, so pros and cons to the service.

I'm in the Windsor camp but that's in terms of thinking about the charm and activities with a hotel near the castle. (I know you said you're not concerned with activities, tho'--have your kids been there?) Your kids are old enough to deal with the late evening arrival, especially since it's a daytime flight, so I wouldn't feel the need to crash at the airport. We enjoyed Macdonald Windsor hotel' & location).

Don't use the Hoppa Bus. A taxi from T2 to the hotels on Bath Road is only around GBP 12-15.

Although I do understand the simplicity of staying near LHR, I would still have to find transportation to either Windsor or London in the AM and then have to make our way back to LHR to collect our luggage and then head to Oxford so I'm ruling that out.

Looking at this strictly from a logistical perspective, to me it seems like the London/Paddington option is easier. Heathrow Express to Paddington, stay at Premier Inn at Paddington, and then GWR direct train from Paddington to Oxford (or coach from Marble Arch). Is this correct? Please let me know if I'm missing something or if you disagree. I'm asking this because I'm not certain so please challenge my theory. Again, I'm posting here to understand the logistics and potential aspects that I'm overlooking.

PS - I really enjoy the process of planning trips and I'm always looking for feedback so let me have it!! LOL!

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My opinion: You would increase the hassle factor and stress greatly by going into London for just 6 hours.....not worth it.
We've been to London many times, and so have you, so what's the big thrill for 6 hours?
Save it for when you and the kids can be there for several days and do it justice.
You may have jet lag the morning you would wake up in London and be dragging anyway.
I'd much rather wake up in Oxford.
Then have a nice breakfast and go for a walk.
Just my opinion, which you did ask for.

I think you are probably correct and this does sound more pleasant and less stressful. Perhaps I have been subconsciously delaying the family time as the next days will be spent with them in the Oxford area and they are not accustomed to guests (especially kids!), I wish we had more time in London but it didn't fit in our plans this trip.

I appreciate you taking the time to answer my questions.

I don't doubt that is the easiest option.

However you could also take your luggage with you from your hotel at 'Heathrow' to Windsor or London. Then put it in an app based left luggage facility (such as Stasher, other companies exist) for the day at either location, then go direct to Oxford without having to return to Heathrow.

If taking the Heathrow Express to Paddington on arrival book as soon as possible to get 'early bird' fares which are cheaper than the Elizabeth Line.

As well as the train to Windsor from 'Heathrow' if you were staying on the Bath Road there is also London Bus #81 to Slough then a very frequent bus service to Windsor on multiple bus lines.