Top 10 prettiest places to visit in Dorset holiday cottages

Top 10 prettiest places to visit in Dorset

Cath C 27 February 2023

With so much natural beauty in Dorset, this county is a popular destination of choice for those wanting to escape the everyday. 

Immerse yourself in the past by visiting a wealth of historic castles, explore endless miles of unspoilt countryside, enjoy wonderful seaside towns and villages like Swanage and Weymouth or spend lazy days on the beach with the sand between your toes. 

We have compiled a list of the 10 prettiest places to visit whilst in Dorset to make sure you get as much from your staycation as possible…

Durdle Door


Durdle Door is one of Dorset’s most photographed and iconic landmarks. It is part of the Jurassic Coast World Heritage Site and is an extremely popular beauty spot too. It was created when the sea pierced through the limestone around 10,000 years ago. The coastline is of such international geological importance that it was designated England’s first natural World Heritage Site by UNESCO in 2001 and is now part of a family of natural wonders including America’s Grand Canyon and Australia’s Great Barrier Reef.

It is accessible from above via a car park and the South West Coast Path, from which it is a 15-minute walk to the view point and then another 140-plus steps down onto the beach. Durdle Door is just one of the great places to visit in Lulworth - why not seek out a few more during your stay?

Where to stay nearby

For couples: The Cowshed (sleeps 4)

For familiesSea Thrift  (sleeps 6)

For groups: The Old Forge (sleeps 8)

Corfe Castle

The dramatic ruins of Corfe Castle are situated halfway between Wareham and Swanage and no trip to the Isle of Purbeck would be complete without a visit to this picturesque village. Corfe Castle stands on a natural hill overlooking the village and guarding the main route through the Purbeck Hills; it can be seen from miles around from all directions.

Corfe Castle was constructed by William the Conqueror in the 11th century and is one of Britain's most iconic and evocative survivors of the English Civil Wars, partially demolished in 1646 by the Parliamentarians. Nowadays, Corfe Castle is owned by the National Trust and is open to the public with daily tours available too.

The village is easily accessible by public transport and is a stop on the Swanage Railway. Click here and discover even more things to do in Corfe Castle too!

Where to stay nearby

For couples: Honeypot Cottage - Corfe Castle (sleeps 4)

For families: Rose Castle Cottage (sleeps 5)

For groups: St Edmunds House (sleeps 8)

Lulworth Cove


Lulworth Cove is world famous for its beautiful beach and clear blue water, surrounded by unique geology and landforms including Lulworth Crumple and Stair Hole. Whilst here, a visit to the Lulworth Cove visitor centre is worthwhile for a better appreciation of the outstanding geology.

Lulworth Cove is one of the highlights of the Jurassic Coast, a designated World Heritage Site. The rock arch of Durdle Door is just a 10-minute drive away or a breath-taking 30-minute walk along the coastal path. Did you know, Stair Hole is reputed to be the inspiration for the location of Enid Blyton’s book, The Rubadub Mystery

Click here and discover some of our other favourite things to do at Lulworth Cove too!

Where to stay nearby

For couples: Carefree Cottage (sleeps 4)

For families: Sea Holly (sleeps 6)

For groups: Moonfleet (sleeps 10)

Highcliffe Castle


Located just 3 miles from Christchurch, Highcliffe Castle has been described as arguably the most important surviving house of the Romantic and Picturesque style of architecture, which flourished towards the end of the 18th century. Its significance is recognised nationally by its Grade I status on the Statutory List of Buildings of Special Architectural and Historical Interest. 

The grounds surrounding Highcliffe Castle are perfect for a stroll or family picnic on the lawns. There is also direct access to a wonderful sandy beach and the unspoilt nature reserve of nearby Steamer Point. Within the grounds, there are tearooms too which serve hot and cold drinks along with delicious snacks and homemade cakes. 

Where to stay nearby

For couples: Chewton Den (sleeps 2)

For families: Daisy Cottage (sleeps 4)

For groups: Island View (sleeps 12)

Old Harry Rocks


Old Harry Rocks are brilliant chalk-white arches, stacks and stumps, jutting out into the sea and running along the ocean on Handfast Point, at the southern end of Studland Bay. Although the whole area is known as Old Harry Rocks, Old Harry refers to the single stack of chalk standing furthest out to sea. Until 1896, there was another stack known as Old Harry’s Wife, but erosion caused her to tumble into the sea, leaving just a stump.

These chalk formations are popular with both walkers and cyclists and this area is part of the South West Coast Path. From the rocks, you can enjoy views across the water to Poole and Bournemouth. On a clear day, you can even see The Needles (another well-known chalk rock formation) on the Isle of Wight. Check out our ultimate guide to the Dorset coast here for more inspiration! 

Where to stay nearby

For couples: Old School House (sleeps 2)

For families: Heath Lodge (sleeps 7)

For groups: Chalross (sleeps 10)



Located near the Wiltshire border, Shaftesbury is a small market town with a fascinating history going back to the Saxon times. The town is the home of Gold Hill, a steep cobbled street lined with pretty cottages (made famous by the Hovis bread advert) and has magnificent views over Thomas Hardy’s Blackmore Vale.  

The town is a lovely place to spend an afternoon and stroll around with a variety of independent shops, restaurants and cafes here.

Where to stay nearby

For couples: No 1 Curwens (sleeps 2)

For families: Bears Den (sleeps 6)

For groups: Chase House (sleeps 17)

Brownsea Island


Brownsea Island can be found inside Poole Harbour – which is one of the largest natural harbours in the world – and is only accessible via boat from either Poole Quay or Sandbanks. Brownsea Island is a nature reserve owned by the National Trust, and one of the only places in the UK where you can spot red squirrels, which are very scarce and endangered on the mainland. 

With dramatic views to the Purbeck Hills, Brownsea Island is a haven for wildlife with a huge variety of birds, including the sandwich tern, peacocks and hens. There is also a café serving hot and cold drinks, lunches, cakes and ice cream as well as natural play area, trails, visitor centre and daily guided tours (subject to volunteer availability).

Where to stay nearby

For couples: The Studio Barn (sleeps 2)

For families: Woodridings (sleeps 8)

For groups: Hilltop Harbour View (sleeps 14)

Kingston Lacy


Kingston Lacy is an elegant 17th-century Italianate mansion, set in attractive formal gardens and extensive parkland, now owned by the National Trust. The mansion was once owned by William John Bankes, but after being caught in an ‘illicit act’ with a guardsman at a time when being gay was punishable by death, he was forced to exile himself and spent the last 14 years of his life abroad. 

Whilst he travelled, he collected art and furniture, and had it all sent back to the family home, Kingston Lacy, creating a fabulous collection with a surprising history. These paintings included those by Rubens, Van Dyck, Titian and Brueghel as well as the largest private collection of ancient Egyptian artefacts in the UK.

The Kingston Lacy Estate stretches for 8,500 acres and takes in Holt Heath National Nature Reserve and Badbury Rings. There are 12 way-marked footpaths around the estate and the National Trust runs regular guided walks.Click here and discover some of our other favourite National Trust places to visit too!

Where to stay nearby

For couples: Dorset View (sleeps 2)

For families: The Hayloft - Winterborne Zelston (sleeps 4)

For groups: Drongstyle Cottage (sleeps 5)



Swanage is a pretty, coastal town and within striking distance of most Dorset attractions. Swanage has been one of England’s iconic seaside resorts since the Victorian era and, to this day, retains much of its Victorian-style architecture. The seafront is home to an array of colourful beach huts, making Swanage a textbook example of the best of the English coast.

Swanage Bay Beach is at the heart of the town and its golden sands and clean sea are always a hit with families. There’s no shortage of things to do here either - hire out a deckchair or beach hut for ultimate relaxation or hop in a kayak or pedalo in the water for a mini aquatic adventure. 

For more inspiration, read our blog post on the top ten things to do in Swanage.

Where to stay nearby

For couples: Porthole Penthouse (sleeps 2)

For families: Seaside Cottage (sleeps 6)

For groups: Providence Terrace (sleeps 8)



Weymouth is a beautiful seaside resort and popular holiday destination. Weymouth was made famous over 200 years ago by none other than King George III himself, who visited the seaside town often to bathe in its waters, which were said to have medicinal powers.

Weymouth was also home to the sailing events in the 2012 London Olympics and has since seen become popular for its sports scene. Weymouth is just a stone’s throw away from the beautiful Isle of Portland and right next to the world-famous Chesil Beach. Chesil Beach is part of the Dorset AONB and has lots of wildlife and natural beauty to discover.

Chesil Beach was made popular by Ian McEwan’s novella On Chesil Beach with beautiful scenes of the beach featured in the 2017 film adaptation of the book. 

For even more inspiration, read our blog post on the top ten things to do in Weymouth.

Where to stay nearby

For couples: Dragonfly (sleeps 4)

For families: Sun Beam (sleeps 6)

For groups: Cowleaze Cottage (sleeps 8)

Map of Dorset's prettiest places

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Plan your visit to Dorset

Have you been inspired to visit Dorset and some of the region’s prettiest places for yourself? To inspire your Dorset adventures further, you may also enjoy the best beaches in Dorset to visit and Dorset coastal walks

Disclaimer: Whilst every effort has been made to ensure the accuracy of the information at the time of writing, please ensure you check carefully before making any decisions based on the contents within this article.

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