Great town to work remotely in for 2 weeks - maybe Cotswolds?

Well, I almost didn’t add this because it’s not England (which I missed the first time I read through), but maybe take a look at Tallin. It won’t be crowded and has all you have mentioned (except the England part). And it will most likely be nicer temps and cheaper. I stayed 5 nights solo last Sept. in an apartment and really liked it.

Swansea, Wales. It's a mid-size town (approximately 240,000 people), the city is walkable, a train can be taken to England (including London, a trek I took) and it has pleasant shops and eateries. Swansea has incredible views of the ocean. It's green and beautiful. Swansea struck me as a peaceful town, so it will aid concentration. Sorry, I don't have any accommodations to recommend, but Lonely Planet and Rick Steves will have plenty. It sounds like you enjoy books because you mentioned book stores. Swansea as the home of poet Dylan Thomas has literary heritage.

I would suggest that the Cotswolds would not be a great location for your plan, mainly because there is really only one train line that goes through them with only one station that could be classed as a town, which is Moreton-in Marsh. It’s not the prettiest place in the Cotswolds and getting around without a car will mean grappling with local bus services.

But there are loads of places that could fit your brief. Off the top of my head here are a few suggestions, although I’m sure others will come up with more.

Maybe larger than you suggested - Chester, York, Oxford and Cambridge.

Places I particularly like - Ludlow, Lewes, Whitby, Lancaster, Kendal.

Places I don’t really know but hear good things about - Salisbury, Rye.

Not the Cotswolds, but Cockermouth on the edge of the Lake District might suit you.
It doesn't have a railway station, but has pretty good bus services and is only 30 minutes or so from Keswick. It is quite a foodie town, with quite a few good pubs.
It has a bookshop in the form of The New Bookshop, and Wordsworth House Museum.
Lots of walks actually within the town and lots more in the local area.

I'm not sure what moderate rate translates to in £ (or $), in terms of suggesting places to stay. It is pretty short notice in the UK in high season. What sort of accommodation do you want - self catering, guest house, b and b?

Wow, these are all really good suggestions! Thank you! I will check out Wales! And also those other English towns.....now I'm thinking maybe Oxford would suit. (Talinn is also a GREAT idea -- I've been and have spent a couple weeks there. I agree that it's wonderful - also Parnu is fantastic in Estonia).

Many thanks, everyone!

The Cotswolds will be crowded the last two weeks in August.

In the UK, I'd suggest somewhere in Devon or Cornwall

Cardiff, Wales

Anywhere in the Highlands of Scotland if you can find accomodations and are willing to buy spray for the midges.

My suggestions outside the UK

Riga, Latvia

Vienna, Austria

Torshavn, Faroe Islands

Helsinki, Finland

Rovaniemi, Finland

Luxembourg City, Luxembourg

It may be worth checking what phone signal and data rate is available wherever you choose. Lots of the Cotswolds are what is known as "NOT-spots". Don't count on strong 5G, or even weak 3G. I often just get E, totally useless for data transfer.

You may well find a good strong signal - all depends. Just suggesting you check.

In these circumstances, I always recommend using your preferred site for accommodation (booking.com, AirBnB, whatever you like). Fill in your dates, budget and other general requirements (wifi, dedicated work space, etc) and set the map to include your areas of interest. Scroll through the results to see what catches your eye.

I’d select a neighborhood of London. One with a Premiere Inn or Travel Lodge. Somewhere like Richmond or Clerkenwell, Hampstead or Shoreditch or Ealing.

Don't discount the idea of Inverness. Weather is good in August, night life is good without being too boisterous, and there is great food. Walks along the Caledonian Canal are peaceful and full of natural beauty.

Tallinn, Stockholm and Copenhagen are also great ideas in August.

I'm going to vote for Lewes, East Sussex. It's an hour's train ride away from London. You can take the train to Brighton, Seaford, Rye, and Hastings (amongst others). It's very walkable. They have good public transportation. You can walk to the supermarket and several bookstores. It is beautiful.
I'm a middle-aged woman who travels solo.
Feel free to PM me if you'd like to talk/learn more.

Maybe Bath for a larger town, or for somewhere smaller you could look at Bradford on Avon. It’s a very short train ride from Bath and is a small town with plenty of food options and easy walking along the river.

I've been thinking a lot about this one. I agree the Cotswolds wouldn't be suitable for someone without a car- you'd be beholden to infrequent bus service to get around. I like the idea of being on the coast, especially in summer- the north Norfolk coast is beautiful, and Cromer has a train station and bus service connecting to the rest of the coast. There are lots of nice seaside towns in Kent- I think my favourite is Whitstable, where you can rent a fisherman's cottage on the beach (tho I think you might be too late for that this time of year). I'd also look at Dorset (especially Weymouth), and see what's available in Devon/Cornwall (which gets very full of domestic travellers in summer). I really like the suggestion of Whitby above- anywhere along the NE coast, all the way up to Berwick-upon-Tweed, will be very nice this time of year. Like others have suggested the best may be to just see what's available and be guided by that- but my general suggestion is to look on the coast. And definitely you won't find accommodation in Edinburgh this month- everything will have been booked up months ago unfortunately. Good luck deciding.

In the Cotswolds, I recommend The Volunteer Inn at Chipping Campden.
It has the best pub in town and a great Indian restaurant. Room rates are not high and rooms are spacious.

Consider Winchester in Hampshire. It ticks a number of the boxes you mentioned.

I remember someone a few years back made the news because they did this, told a government official, and got deported. I assume with the change in technology and working norms. that the UK and others have exempted this from the work visa requirement? Would be crazy not to.

I'm not sure a coastal town, especially in Devon or Cornwall, is the right answer given that you are there over the August bank holiday period, which is a very busy time.
I actually looked at Kendal but because it is a bolt hole for the well informed from the Lake District can't actually find anywhere at a sensible price for the two week period.

With regard to Mr E, he probably is right in theory that this should be on a working visa. I guess that is a bit subjective as you wouldn't be doing a UK job, which someone else (a local) could do, or be being paid in the UK. Grey area may be a better term than subjective.
Somewhere in Scotland could be better (outside Edinburgh, and other heavily touristed areas) as the schools have gone back.

There is Lincolnshire or East Yorkshire, lots of town and village options. I think the main issue will be availability and cost now wherever you look.

I personally love the Cotswolds and think it is the most beautiful place in all of England. I would get a good guide book to help decide which town would meet your needs. Rick Steeves is great Imho. If you don't drive maybe use something like Uber. Another option would be the college towns of Cambridge or Oxford.

I'd be very leery nowadays about taking work and my work computer into another country. Tourist Visas say that you can't work in Europe. With border and immigration tightening in the US and EU, you may want to double check if it's even legally allowed.

I'd also say that it is not as romantic as you think. You will be on a 6 hour time difference and probably not as productive as you would be at home.

Honestly, working while on a "vacation" is not romantic or fun. Family members have had to do it when we've gone on vacation and dealing with the work issues plus the time difference is not just the "watching kids play soccer from balcony". You need a LOT of discipline to stay focused. Honestly, you will probably be half as productive. If it were me, I'd go to a place that I've been before so I wouldn't feel the need to go out and explore.

My experience is very different from Heather's. I took a trip to work remotely and had no problem staying focused. The key is to view what one is doing as a working trip with a different environment in which to work. As for restrictions, I don't believe the UK proscribes working remotely on its soil. A brief trip like the one the OP proposed won't involve a visa.