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 are looking to expand our collection of properties in this area. If you have a property to let, please get in touch to arrange a meeting with one of our Property Managers by calling 01929 422776 or emailing us at bookings@dorsetcottages.com. You can also order your FREE Homeowner Letting Guide here.



11 Properties found
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Weymouth, Dorset Coast

WY437

(No dates selected)

£362 - £791
per week
From £281 for a 3-night stay
  • 4 Star Gold
  • A modern 1 bedroom first floor apartment arranged over two floors in a character property, just a short walk from beach and town.
  • 2 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi
  • On-street parking
  • Parking permit provided
  • Beach 0.1 miles
  • Pub 0.1 miles
New Property

Weymouth, West Dorset

WY455

(No dates selected)

£317 - £631
per week
From £247 for a 3-night stay
  • 3 Star Gold
  • Bumble Bees is a delightful, modern one bedroom ground floor annexe located in a popular area of Weymouth. It has been recently renovated to a high standard with quality finishes throughout. The annex is ideal for couples looking to explore the Jurrasic coast, local cycle routes or the vibrant seaside town of Weymouth!
  • 2 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi
  • Enclosed garden
  • Private parking
  • Beach 2 miles
  • Pub 1 mile

Weymouth, West Dorset

WY435

(No dates selected)

£401 - £885
per week
From £310 for a 3-night stay
  • 4 Star
  • 5 at the beach is a newly renovated property located in one of the many character buildings on Weymouth’s esplanade.
  • 4 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi
  • On-street parking

Langton Herring, West Dorset

WY431

(No dates selected)

£392 - £842
per week
From £303 for a 3-night stay
  • 3 Star
  • 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
  • 1 Bathroom
  • WiFi
  • Enclosed garden
  • On-street parking
  • Open fire or woodburner
  • Beach 5 miles
  • Pub 1 mile
10% Off!

Dorchester, Dorset Countryside

WY408

(No dates selected)

£411 - £886
per week
From £317 for a 3-night stay
  • 3 Star Gold
  • Special offerEnjoy a fabulous 10% off a stay at Ruth's taken up to the end of November 2019!
  • 4 Guests
  • 2 Bedrooms
  • 1 Pet
  • 1 Bathroom
  • WiFi
  • Garden
  • Enclosed garden
  • Private parking
  • Beach 9 miles

Weymouth, Dorset

WY436

(No dates selected)

£461 - £1000
per week
From £355 for a 3-night stay
  • 4 Star
  • 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
  • No Pets
  • 1 Bathroom
  • WiFi
  • Enclosed garden
  • On-street parking
  • Beach 1 mile

Weymouth, West Dorset

WY434

(No dates selected)

£401 - £885
per week
From £310 for a 3-night stay
  • 4 Star
  • 4 at the Beach is a stunning contemporary first floor flat located right on Weymouth beach front
  • 4 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi
15% Off!

Weymouth, Dorset

WY394

(No dates selected)

£418 - £901
per week
From £323 for a 3-night stay
  • 4 Star
  • Special offerEnjoy a fantastic 15% off a full weeks stay during October 2019 at this lovely house!
  • 4 Guests
  • 2 Bedrooms
  • 1 Pet
  • 1 Bathroom
  • WiFi
  • Garden
  • Enclosed garden
  • Private parking
  • Beach 5 miles
  • Pub 2 miles

Weymouth, Dorset Coast

WY406

(No dates selected)

£398 - £865
per week
From £308 for a 3-night stay
  • 3 Star
  • 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
  • 1 Bathroom
  • WiFi
  • Private parking
New Property

Weymouth, Dorset Coast

WY458

(No dates selected)

£481 - £1035
per week
From £370 for a 3-night stay
  • 4 Star
  • Fisherbridge is the perfect place for a family get away, located close to the beach and local shops you have plenty to do on your doorstep!
  • 5 Guests
  • 3 Bedrooms
  • No Pets
  • 1 Bathroom
  • WiFi
  • Enclosed garden
  • Private parking
  • On-street parking
  • Beach 1 mile
  • Pub 0.2 miles

Weymouth, Dorset

WY397

(No dates selected)

£805 - £1794
per week
From £613 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
  • 2 Bathrooms
  • WiFi
  • Garden
  • Enclosed garden
  • On-street parking
  • Beach 2 miles
  • Pub 1 mile