Lake District Towns

We stayed three nights in Keswick and liked it very much, but haven't been in Grasmere or Windermere. My impression is that the Keswick area has fewer visitors and equally good scenery, but doesn't have the Wordsworth and Beatrix Potter associations of the places further south. It's on Derwentwater, a large lake with a tour boat the circles around the shore and stops at various places for hikers to get on and off, making level hikes of various lengths possible. There's also a local bus that makes a loop through some of the passes and around the various hills (which they call fells). Nearby is the Castlerigg Stone Circle, a prehistoric site in a beautiful evocative setting right off the road. There's a pencil museum (lots of lead and slate mining in the area's history) that others have found quite interesting, we didn't spend long there. And also I think a car museum. And a weekly market in the main square. Lots of lodging and dining options.

But you'll get a better read from those who have been in both areas. They're not that far apart, you don't necessarily have to choose.

We did a walking tour from Windermere to Grasmere to Coniston and back to Windermere but haven't visited Keswick. We stayed at the Firgarth Guesthouse in Windermere at the start and end of our tour and would go back again. Firgarth is a short walk to town center and a slightly longer walk to/from the train station. Bus to Grasmere stops across the street from Firgarth if you don't want to do the 3 hour walk to Grasmere. (The scenic walking route through the hillside is longer).
Firgarth, Ambleside Road, Windermere, Cumbria, LA23 1EU
Kirk Allan's Bed and Breakfast, Church Bridge, Stock Lane, Grasmere, Cumbria, LA22 9SN
Bluebird Lodge, Waterhead, Coniston, Cumbria, LA21 8AJ

Windermere is the small big town of the trio, Grasmere and Coniston being small tourist villages. Grasmere know for poet Wordsworth and Coniston for Sir Campbell's Bluebird speedboat. The area is very compact and surrounded by scenic hills with walking paths.

The bunny lady's (Beatrix Potter's) Hill Top farm is across the lake from Windermere. You can take a ferry across the lake. http://www.cumbria.gov.uk/roads-transport/highways-pavements/windermereferry.asp

If you are interested in peak bagging, Helvellyn from Grasmere is the easier ascent than from Patterdale via Striding Edge.

Transportation options:

http://www.lakedistrict.gov.uk/visiting/placestogo/explorewindermere/travelwindermere

If possible, please try to leave the car at home and use public
transport to help keep the Lake District special.

We've been going to the Lake District for years and we always stay in Keswick.
Grasmere is very picturesque and VERY touristy. Nice to visit for a few hours but not where I'd want to stay.
Windermere is at the southernmost end of the Lakes and it is geared to boating and sailing on the lake. Still beautiful but not in the most beautiful part of the area.
Keswick has a lot to offer. It's still a bit touristy but much more "real" than the other two places. It's beautiful and within easy reach of everything you want to do and see in the area. If you have a car parking is relatively easy and, if you don't, the bus service from there is easy to use.