My husband and I are 68 yr. olds who are very active living and hiking in the Canadian rockies. We would like to do a self guided walking trip in the Cotswolds and would like to stay in higher end but more importantly charming accommodations. Any advice on companies who arrange carrying our luggage , providing walking maps and accommodations here ? Also we would like to go in May - is the first week too early to enjoy lots of flowers and comfortable weather ?
We have done several walking/ hiking trips in Europe with various companies and really enjoyed them. Thanks in advance.

I've done a fair amount of walking in the Cotswolds but have never done an 'organized' tour (or any sort of tour for that matter) so I can't help with companies. But a few Fodorites have so hopefully one of them will see your thread. I know there are several well respected firms that do that sort of thing.

As for "Also we would like to go in May - is the first week too early to enjoy lots of flowers and comfortable weather ? " There is absolutely no way to know. May could be just glorious or a total wash out (or some of both throughout the month). Same can be said for any month . . .

Check out Lexma's great trip report. Lots of great information there -
My Wonderful Walking Trip in the Cotwolds

Such walking trips have become popular on social media. I'd do a search on Google or even YouTube for possible additional research and planning. A lot of folks do these on their own, and you may find suggested itineraries and other resources online (such as baggage delivery and such).

hurrygirl, my wife and I (71 and 75, respectively) walked the Cotswold Way in May 2024. The complete trail is 164 km, starting in Chipping Campden and ending in Bath. We chose a nine-night, eight-day itinerary, so daily walks were in the 15 to 25 km range. I would not describe the walking as particularly difficult, but the Cotswold Way follows an escarpment, so you will climb and descend at least once if not twice a day.

Our trip was arranged by Celtic Trails, a well-established and reliable firm based in Wales. They arranged all of our accommodations on the trail, which included breakfasts, and daily luggage transfers, and provided a walking pack that included recommendations for lunches and dinners, 1:25,000 OS maps, as well as the Trailblazer guidebook for the trail. If you look at their website, you'll see that they offer several variants of the Cotswold Way, as well as something they call the Cotswold Round itineraries. https://www.celtictrailswalkingholidays.co.uk

A word about the accommodations: I would not describe their choices as "higher end." I think that part of the reason for this is to manage the price point for clients, but the other factor is that some of these small villages have very few accommodations to choose from. Indeed, in a couple of cases, we were met by a taxi at th end of our walking day and were driven to another village for our accommodation, and then picked up and returned to our previous location the next morning. But if you decide to investigate Celtic Trails options, you could certainly talk to them about your preferences, as they are approachable and responsive

There is another firm that we have used to walk in the UK: Mickledor Travel (https://www.mickledore.co.uk) arranged our walk on the Cumbria Way, which runs 110 km from Ulverston to Carlisle. This is essentially a lower-level walk from south to north through the Lake District, although significantly more difficult than the Cotswold Way. Their services are similar to Celtic Trails, and they do offer Cotswold Way and Cotswold Rounds itineraries. We found them equally reliable and professional, and I would assess their accommodations as being slightly up-market to those arranged by Celtic Trails. But again, some overnight stops offer few choices.

Unfortunately, our favourite walking company, On Foot Holidays, (also UK-based) does not offer any Cotswolds itineraries. They have arranged two walking trips for us in Italy, and they are truly top-notch. If, however, you are tempted to walk elsewhere in the UK, I recommend them without hesitation.

Other posters here, such as Lexma, have made their own arrangements for self-guided walking, and it is clearly do-able (and doubtless less expensive). Speaking strictly for ourselves, we have been happy with firms that set it up in detail.

About walking in May: both our Cumbria Way and Cotswold Way walks were in the month of May. By good fortune, we enjoyed mostly sunny weather with only the occasional shower. But as janisj points out, that really carries little weight in terms of what it would be nest year. As for flowers, absolutely glorious on both walks. I will never forget walking through forest paths lined with wild garlic ... Queens Anne's Lace along the sides of fields, chestnut trees with magnificent candles, and sadly, tons of stinging nettle, which seems to grow beside every stile or kissing gate you will encounter.

Enjoy your travels, from a fellow-Canadian, who thinks in kilometres, not miles.

Thanks so much to you all for your feedback. Especially big thanks to Anhelm for your detailed response. It is very helpful.
Your 15-25 km. / day sounds great for us considering the terrain we think.
🤞we are lucky with weather. We dud the West Highland Way in 6 days of downpour so a sunny walking trip would be especially lovely.

My mom and I took a trip in late May many years ago and the headline in the paper was about the temps being in the "sizzling twenties". It was normal May weather for us!

We were gone for two weeks and there was a little misting of rain as we left the London airport with a rental car and a sprinkling of snow at Loch Lomond. Other than that, beautiful warm weather. I'm returning next week at the same time. I hope I will be so lucky!

My wife and i recently completed a circular walking tour of the smaller Cotswolds villages, beginning and ending in Moreton-in-Marsh. It was one of the best trips we have taken. I highly recommend Celtic Trails walking tours. The map and the walking notes were very detailed and easy to follow. The company was very responsive when we needed to customize our itinerary. Great web site.

Thanks so much for the feedback. We are straggling to decide on which route / villages to do. We will get there