Weymouth and Portland Cottages

Every inch the modern tourist resort, with a wide and shallow sandy beach that in the summer is home to donkey rides, Punch and Judy, sand sculpture and world class local ice cream, Weymouth is in many ways the first great English seaside resort.

Its success owes much to the patronage of King George III who made Weymouth his summer residence in the 1780s and was even known to venture into the sea – almost unheard of in polite society – in a bathing machine. The famous white horse carved into the hill at Osmington dates from 1808 and is said to depict George leaving the town for the last time.

Weymouth has a long history as a port and since 1571 has incorporated neighbouring Melcombe Regis, thought to be the point at which the Black Death came into England in June 1348. In the mid-17th century Weymouth saw heavy fighting during the Civil War and was a major point of departure for settlers bound for the New World.

Before becoming MP for Weymouth in 1702, the architect Sir Christopher Wren controlled the quarries at Portland so in the wake of the Great Fire of London it was an obvious choice to have his showpiece St Paul’s Cathedral built of Portland Stone. By coincidence, Sir James Thornbill, the artist who decorated the inside of St Paul’s was born in the White Hart pub in Melcombe Regis in 1675.

The area more than did its bit during the two world wars of the 20th century, hosting some 120,000 convalescing ANZAC troops during World War One and seeing the embarkation of more than half a million soldiers for the invasion of France in 1944, while the famous bouncing bombs of the Dambusters were tested in the Fleet lagoon at Chesil Beach.

When Portland’s naval base and air station closed at the end of the 1990s it ended more than 500 years of association with the Royal Navy. A geologically important limestone tied island connected to the mainland by the remarkable shingle of Chesil Beach, it is the home of British Sailing with the Weymouth and Portland National Sailing Academy hosting the sailing 2012 Olympic sailing regattas.

About our Weymouth and Portland Holiday Cottages

Our collection of properties in Weymouth and Portland range from family apartments to larger celebration houses, something to suit everyone on your next holiday to Dorset.

Take a little time to browse through our selection of holiday cottages in Weymouth and Portland. We’re certain you’ll find something just right for a truly special Dorset holiday.

Due to high demand from our guests, we have recently started looking for properties in this area. If you have a property and are considering letting, please get in touch with Claire, our property manager on 01929 448694 or email c.macdonald@dorsetcottages.com



7 Properties found
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Weymouth, Dorset

WY436

(No dates selected)

£425 - £945
per week
From £319 for a 3-night stay
  • Casa Merocca is a quaint stone fronted terraced house situated in a residential street, just a stone’s throw away from Weymouth’s historic harbour. Great for a family holiday providing an excellent base to discover the Jurassic Coast and Dorset Countryside.
  • 4 Guests
  • 2 Bedrooms
  • WiFi
  • Beach 1 mile

Weymouth, Dorset

WY397

(No dates selected)

£769 - £1707
per week
From £577 for a 3-night stay
  • 4 Star
  • Perfect for a family get-together or a group of friends.  This immaculately presented five bedroom house has a welcoming, sociable and fun feel.
  • 8 Guests
  • 5 Bedrooms
  • 1 Pet
  • WiFi
  • Beach 2 miles
  • Pub 1 mile

Weymouth, Dorset

WY406

(No dates selected)

£362 - £805
per week
From £272 for a 3-night stay
  • Situated just a short walk from Bowleaze Coveway, a popular beach to the East of Weymouth, Bowleaze Beach Apartment is a spacious two bedroom first floor apartment, with a view of the sea, and private off road parking.
  • 4 Guests
  • 2 Bedrooms
  • 2 Pets
  • WiFi
  • Private Parking

Weymouth, Dorset

WY394

(No dates selected)

£382 - £848
per week
From £287 for a 3-night stay
  • Rose Cottage is a pretty two bedroom cottage, with a cosy, welcoming feel. Situated in Weymouth, approximately 4 miles from the town centre and beach.
  • 4 Guests
  • 2 Bedrooms
  • 1 Pet
  • WiFi
  • Private Parking
  • Beach 5 miles
  • Pub 2 miles

Langton Herring, Dorset

WY431

(No dates selected)

£356 - £790
per week
From £267 for a 3-night stay
  • Badgers Cottage is situated in the heart of Langton Herring Village, a stone’s throw from the Elm Tree Inn and within easy access of Fleet Lagoon and beyond. An ideal base for a family wanting to explore the Dorset coast and countryside.
  • 4 Guests
  • 2 Bedrooms
  • 1 Pet
  • WiFi
  • Beach 5 miles
  • Pub 1 mile
  • Open fire or woodburner

Langton Herring, Dorset

WY430

(No dates selected)

£627 - £1393
per week
From £470 for a 3-night stay
  • A lovely stone cottage in the Village of Langton Herring offering spacious accommodation for family or groups of friends near to local amenities. A wonderful base for exploring the Dorset countryside and coast.
  • 6 Guests
  • 3 Bedrooms
  • 2 Pets
  • WiFi
  • Private Parking
  • Beach 5 miles
  • Open fire or woodburner

Dorchester, Dorset

WY408

(No dates selected)

£375 - £833
per week
From £281 for a 3-night stay
  • 3 Star Gold
  • The perfect family cottage, located in the picturesque village of Charminster, just 2 miles from the county town of Dorchester, and 6 miles from Cerne Abbas, home of the Cerne Abbas giant.
  • 4 Guests
  • 2 Bedrooms
  • 1 Pet
  • WiFi
  • Private Parking
  • Beach 9 miles