Author: Hayley Oats from Dream Cottages

Despite wanting to cosy up, Winter provides a golden opportunity to see some of the most breath-taking views of the Jurassic Coast, England’s only natural World Heritage Site.

Join Dream Cottages as we grab our walking boots and delve into the Top Winter Walks, with cosy cottages to stay in en route.

Back to Blog

Old Harry Rocks Walk

Some of the best Winter Walks in Dorset are along the South West Coast Path and take in stunning natural geological formations, such as Durdle Door and Lulworth Cove.

Further along, there are the instantly recognisable chalk sea stacks of Old Harry Rocks.

A Winter Walk along the clifftop facing Old Harry Rocks will reward you with views across Poole Harbour to Bournemouth and the Isle of Wight. Stop off for some much deserved pub grub at the Bankes Arms pub in Studland which completes this clifftop stroll.

View cosy cottages in this area

old harry rocks
Old Harry Rocks, near Swanage on the Jurassic Coast.

Langdon Hill Walk

To really make the most of the beautiful seasonal colours, a woodland walk simply cannot be beaten.

Embark on a woodland walk through Langdon Hill woodland on the Golden Cap Estate in west Dorset, entirely rich in wildlife and with glorious coastal and countryside views.

Park up at Langdon Hill car park in Morcombelake (free for National Trust members) near Bridport and begin your stroll. If you are lucky you will see buzzards and ravens soaring overhead.

View cosy cottages in this area

langdon hill woods
Langdon Hill Woods in west Dorset.

The Weymouth and Portland Legacy Trail

Weymouth and Portland hosts some gorgeous scenery, including plenty of pubs along the way!

This 20km long trail from Littlemoor through to Portland Bill makes for a beautiful scenic stroll. The walk includes ten circular walks from various spots along the way.

View cosy cottages in this area

The Isle of Portland on the Jurassic Coast.

Corfe Castle Circular Walk

As well as the stunning natural wonders of landscape and wildlife, Dorset is also rich in human history.

A walk around the majestic Corfe Castle in Purbeck is the perfect excuse not only to enjoy the green rolling landscape which surrounds the ruins, but also to stop off in the pretty village of Corfe.

This quaint historic village is a lovely place to finish your walk and reward yourself with a pint of local ale, or a traditional cream tea.

View cosy cottages in this area


corfe castle
Corfe Castle in Purbeck, Dorset.

Dog Friendly Holidays

No Winter Walk is complete without man’s best friend. So if you’re looking to bring your pooch along on holiday, don’t forget to view our dog friendly cottages.

If you are looking for a holiday cottage in Dorset, then the county has plenty to offer. A holiday cottage in Dorset can give you the perfect opportunity to really explore this diverse county – to sample its award-winning food and explore its abundance of rural charm, tradition and renowned beauty.

cottage and dog
Dog friendly cottages are available.