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Dorset’s towns undoubtedly make great holiday locations. Every town in Dorset has something to offer, whether it is a picturesque and calm escape, or a fun-filled activity holiday.

Dream Cottages will soon be adding a town guide to our website to help you make your decision about what towns to visit on your vacation. In the meantime though, take a look at the 5 towns that we think, under any circumstances, should not be missed!


Weymouth is located about halfway along the Jurassic Coastline and is a popular seaside tourist resort.

Weymouth Beach is a particular hot-spot for holiday makers. It has a beautiful, lifeguarded stretch of sandy beach that offers traditional activities, like Punch and Judy shows and donkey rides, perfect for British summer holidays!

Not only can visitors participate in classic seaside activities, Weymouth Bay is rich in history and heritage, the Nothe Fort and Sandsfoot Castle are definitely worth a visit!

The Bill (1)


The Isle of Portland is situated on the Jurassic Coastline, 5 miles south of Weymouth, and is actually the most southern point of Dorset.

At the most southern point of Portland itself stands the impressive Portland Bill Lighthouse, guided tours of which are offered to visitors.

Well known for being an explorer’s island, Portland is home to an abundance of interesting wildlife and beautiful countryside. It is the perfect place to thoroughly enjoy the outdoors.

Harbour at West Bay

West Bay

West Bay, or Bridport Harbour, is situated approximately 1.5 miles south of Bridport on the Jurassic Coastline.

West Bay is also a fabulous seaside tourist destination, suitable for coast and countryside walks, fossil hunting, fishing and water sports.



The civil Parish of Osmington is situated on the Jurassic coast, 5 miles east of Weymouth, and is a beautiful village in West Dorset.

Home to the Osmington White Horse (an 1808 carving of King George III riding a horse), Osmington is a place of historical interest.

In addition, Osmington Village has a number of pretty country lanes that lead to spectacular open countryside and is simply perfect for country village walks.

Burton Bradstock (12)>

Burton Bradstock

Burton Bradstock village is situated approximately 2.5 miles southeast of Bridport and is one of the main gateways to the Jurassic Coast.

As a result of being so near the Jurassic Coast, the village features vertical cliffs that reach up to 45 metres high!

The village itself is very small and quaint, featuring a number of fascinating 16th- and 17th-century thatched cottages, as well as a reading room and a parish church dating back to the late 14th or early 15th century.