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, West Dorset

WY437

(No dates selected)

£362 - £791
per week
From £281 for a 3-night stay
  • 4 Star Gold
  • 3 By the Sea is a newly renovated first floor apartment, located in one of the character buildings just a few steps away from Weymouth’s famous beach, an excellent town base with all the local amenities on the doorstep. This lovely one bed apartment which is arranged over two floors, offering everything you need to enjoy your stay.
  • 2 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi
  • On-street parking
  • Parking permit provided
  • Beach 0.1 miles
  • Pub 0.1 miles

Weymouth, Dorset

WY455

(No dates selected)

£317 - £631
per week
From £247 for a 3-night stay
  • 3 Star Gold
  • BumbleBees is a delightful, beautifully refurbished one bedroom annexe located in the popular area of Broadwey, Weymouth. It is perfectly located for couples looking to explore the historic Jurassic coast, the vibrant seaside town of Weymouth or even take in the scenery on local cycle routes. 
  • 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. An excellent base in this popular seaside resort with its vast array of shops, restaurants, bars and attractions right on the doorstep.
  • 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

Dorchester, West Dorset

WY408

(No dates selected)

£411 - £886
per week
From £317 for a 3-night stay
  • 3 Star Gold
  • Ruth’s is a converted detached coach house which lies in the centre of Charminster, a village steeped in history and at the centre of a Conservation Area. This perfect family cottage, which is cosy in the winter and airy in the summer, is just 2 miles from the county town of Dorchester, and 6 miles from Cerne Abbas, home of the iconic Cerne Abbas giant.
  • 4 Guests
  • 2 Bedrooms
  • 1 Pet
  • 1 Bathroom
  • WiFi
  • Garden
  • Enclosed garden
  • Private parking
  • Beach 9 miles

Weymouth, West 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. This newly renovated property has fabulous panoramic views across the bay. An ideal base in the heart of this bustling seaside resort with a choice of attractions, shops and restaurants. Perfect for exploring Dorset’s Jurassic coast and countryside.
  • 4 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi

Weymouth, West Dorset

WY394

(No dates selected)

£418 - £901
per week
From £323 for a 3-night stay
  • 4 Star
  • Rose Cottage is a pretty holiday cottage situated in a popular residential area of Weymouth, approximately 4 miles from the town centre and beach. You can enjoy taking in the local scenery on many cycle routes and coastal walks, take a trip into the nearby seaside town of Weymouth or even catch the bus along the Jurassic Coastline!
  • 4 Guests
  • 2 Bedrooms
  • 1 Pet
  • 1 Bathroom
  • WiFi
  • Garden
  • Enclosed garden
  • Private parking
  • Beach 5 miles
  • Pub 2 miles

Weymouth, West Dorset

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 first floor two bedroom apartment, with a view of the sea, and private off road parking. It is perfectly positioned to enjoy Weymouth, Portland and the Jurassic coast, whilst also having so much to do right on your doorstep! 
  • 4 Guests
  • 2 Bedrooms
  • 2 Pets
  • 1 Bathroom
  • WiFi
  • Private parking

Weymouth, Dorset

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, West 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. Laurel House is located approximately 1.3 miles from the main beach at Weymouth. 
  • 9 Guests
  • 5 Bedrooms
  • 1 Pet
  • 2 Bathrooms
  • WiFi
  • Garden
  • Enclosed garden
  • On-street parking
  • Beach 1.5 miles
  • Pub 0.1 miles