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



10 Properties found
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Weymouth, Dorset

WY436

(No dates selected)

£425 - £964
per week
From £319 for a 3-night stay
  • Special offerLast minute discount! 10% off bookings starting within 14 days
  • 4 Guests
  • 2 Bedrooms
  • No Pets
  • WiFi
  • Beach 1 mile
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Weymouth, Dorset

WY437

(No dates selected)

£338 - £765
per week
From £254 for a 3-night stay
  • Special offerLast minute discount! 10% off bookings starting within 14 days
  • 2 Guests
  • 1 Bedroom
  • No Pets
  • WiFi
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Weymouth, Dorset

WY434

(No dates selected)

£358 - £811
per week
From £269 for a 3-night stay
  • 4 Star
  • Special offerLast minute discount! 10% off bookings starting within 14 days
  • 4 Guests
  • 1 Bedroom
  • No Pets
  • WiFi
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Weymouth, Dorset

WY435

(No dates selected)

£358 - £811
per week
From £269 for a 3-night stay
  • 4 Star
  • Special offerLast minute discount! 10% off bookings starting within 14 days
  • 4 Guests
  • 1 Bedroom
  • No Pets
  • WiFi
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Langton Herring, Dorset

WY431

(No dates selected)

£356 - £806
per week
From £267 for a 3-night stay
  • Special offerLast minute discount! 10% off bookings starting within 14 days
  • 4 Guests
  • 2 Bedrooms
  • 1 Pet
  • WiFi
  • Beach 5 miles
  • Pub 1 mile
  • Open fire or Woodburner
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Langton Herring, Dorset

WY430

(No dates selected)

£627 - £1393
per week
From £470 for a 3-night stay
  • Special offer10% SPECIAL OFFER IF YOU BOOK AT AUDREY'S COTTAGE BEFORE THE END OF MAY 2019!
  • Special offerLast minute discount! 10% off bookings starting within 14 days
  • 6 Guests
  • 3 Bedrooms
  • 2 Pets
  • WiFi
  • Private parking
  • Beach 5 miles
  • Open fire or Woodburner
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Dorchester, Dorset

WY408

(No dates selected)

£375 - £850
per week
From £281 for a 3-night stay
  • 3 Star Gold
  • Special offerLast minute discount! 10% off bookings starting within 14 days
  • 4 Guests
  • 2 Bedrooms
  • 1 Pet
  • WiFi
  • Private parking
  • Beach 9 miles
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Weymouth, Dorset

WY397

(No dates selected)

£769 - £1758
per week
From £577 for a 3-night stay
  • 4 Star
  • Special offerLast minute discount! 10% off bookings starting within 14 days
  • 8 Guests
  • 5 Bedrooms
  • 1 Pet
  • WiFi
  • Beach 2 miles
  • Pub 1 mile
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Weymouth, Dorset

WY406

(No dates selected)

£362 - £829
per week
From £272 for a 3-night stay
  • 3 Star
  • Special offerLast minute discount! 10% off bookings starting within 14 days
  • 4 Guests
  • 2 Bedrooms
  • 2 Pets
  • WiFi
  • Private parking
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Weymouth, Dorset

WY394

(No dates selected)

£382 - £865
per week
From £287 for a 3-night stay
  • 4 Star
  • Special offerLast minute discount! 10% off bookings starting within 14 days
  • 4 Guests
  • 2 Bedrooms
  • 1 Pet
  • WiFi
  • Private parking
  • Beach 5 miles
  • Pub 2 miles