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.

The cottage takes one dog per booking, and dogs 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.