Shepherd Oak, Upwey

Shepherd Oak is a smartly converted cottage in Upwey, a village three miles inland from Weymouth, with a stream close by and footpaths leading off in most directions. It is the sort of place people book for the quiet and rebook for the walking: Weymouth's beaches are a short drive away, and Lulworth Cove, Durdle Door and Chesil Beach all sit inside about half an hour.

One well behaved dog is welcome and must be kept on a lead when outside. If you have a day planned where a dog cannot come, nearby kennels can be hired by arrangement with the owner, which is an unusual and useful thing for a small cottage to offer. Guests arrive to find dog bowls already out, and the walking is what comes up in almost every report from an owner who has stayed: the brook the dog can paddle in, the open country around the village, and dog-friendly beaches within reach for a proper run.

Two things to plan for. The upstairs is open to the room below, so there is no easy way to keep a dog out of the bedroom area if you would rather they slept downstairs; bring a crate or a gate if that matters. And the cottage is priced towards the top of its bracket, particularly for a short stay, with no welcome pack, which has disappointed guests used to finding milk and bread on arrival.

Otherwise the reports are consistently good: clean, thoughtfully designed, everything in working order, and an owner who turns up quickly when something needs fixing. There is a pub with a beer garden about ten minutes' walk away, and a bus route into Weymouth for car-free days. Finding the cottage after dark takes some care, as the lane is not well signed.

Shepherd Oak suits one dog and owners who want a comfortable village base for coast and countryside walking near Weymouth, and who do not mind their dog having the run of the whole cottage. It earns a 4.7/5 paw rating.