Weymouth Holiday Cottages

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Your Weymouth, Dorset search returned 269 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published
A brick and white semi detached house with bay windows and potted plants outside at Anchor House Weymouth
Offer
1 of 68
5
Weymouth, Dorset, DT4
  • Sleeps15
  • Bedrooms6
  • Pet FriendlyYes

    4.5★

    Outstanding

  • Sykes rating

Anchor House is a stunning, pet-friendly townhouse with a private hot tub in the heart of Weymouth, Dorset, close to local amenities and the beach. Dorchester 7.8 miles; Bridport 19.9 miles. (Ref. 1105510)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

  • 15% off - Mon 13th Jul to 31st Dec 2026


for 7 nights From £1648

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93 Abbotsbury Road - 1196618 - photo 1
1 of 30
5
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

  • Sykes rating

93 Abbotsbury Road is a bright pet-friendly house resting in Weymouth, Dorset, boasting an enclosed garden and proximity to local amenities and the beach. Dorchester 8.1 miles; Bridport 17.8 miles. (Ref. 1196618)

  • Pets go free
  • Wi-fi
  • Dishwasher


for 7 nights From £717

Last booked yesterday
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A house exterior with brick wall and front door at Pixie Cottage in Weymouth
New property
1 of 26
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

  • Sykes rating

Pixie Cottage is a charming terraced cottage in Weymouth, Dorset, featuring an open-plan living space, enclosed courtyard, and close to beach and harbour. Dorchester 8.7 miles; Dorset National Landscape 9.5 miles; Charmouth 25.4 miles. (Ref. 1203676)

  • Pets go free
  • Wi-fi
  • Washing machine


for 7 nights From £535

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A street with colorful buildings and lampposts at Apartment 1 Brewers Quay in Weymouth
1 of 5
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms1
  • Pet FriendlyNo

  • Sykes rating

Apartment 1 Brewers Quay is a stylish property in Weymouth’s historic Quayside, boasting modern interiors and allocated parking. Dorchester 8.6 miles; Bridport 19.3 miles. (Ref. 1166031)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £456

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Exterior view of a stone and brick house with multiple windows and blue doors a patio with chairs a table and an umbrella and plants at The Gables in Brewers Quay Harbour
1 of 18
5
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms4
  • Pet FriendlyYes

    4.4★

    Good

  • Sykes rating

Lovely 4 bedroom house in gated area. Close to Weymouth harbour. Secure gated parking for one car. Welcomes two dogs. WiFi. (Ref. 994213)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £839

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A stone building with white framed windows and a door along a paved street in a residential area at Brewers Retreat in Weymouth
1 of 22
5
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.5★

    Outstanding

  • Sykes rating

A lovely one-bedroom holiday home perched on the outskirts of Weymouth, Dorset. Romantic. Near a beach. Pet-free. Close to amenities. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1114655)

  • Wi-fi
  • Washing machine


for 7 nights From £528

Last booked yesterday
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A row of terraced houses with different colored facades along a street at Old Harbour Townhouse in Weymouth
1 of 31
5
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.5★

    Outstanding

  • Sykes rating

Old Harbour Townhouse, a delightful, three-storey abode set in the seaside town of Weymouth in Dorset. Near coast. Woodburning stove. Open-plan. Near pub. Dorchester 8.7 miles; Bridport 19.4 miles. (Ref. 1159836)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £702

Last booked yesterday
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A living room with a sofa and television at Ocean Breeze in Weymouth
New property
1 of 29
5
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

  • Sykes rating

Ocean Breeze is a welcoming first-floor apartment settled into the bustling seaside town of Weymouth, Dorset, with open-plan living and close by amenities. Fortuneswell 5.2 miles; Dorchester 7.9 miles; Dorset National Landscape 9.6 miles. (Ref. 1204862)

  • Pets go free
  • Wi-fi


for 7 nights From £599

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A narrow street with houses on the right and a brick wall with plants on the left at Firkin Cottage Brewers Quay Harbour
1 of 22
5
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms4
  • Pet FriendlyNo

    4.5★

    Outstanding

  • Sykes rating

Comfortable renovated cottage with rear garden and close to the town centre. Garden with furniture. Pub 5 mins. Beach 1 mile. Dorchester 9 miles. (Ref. 994191)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £572

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A window seat with two mugs and a muffin on a tray overlooking a carousel and seaside at Shore View in Weymouth
1 of 55
5
Weymouth, Dorset, DT4
  • Sleeps10
  • Bedrooms5
  • Pet FriendlyYes

    4.5★

    Outstanding

  • Sykes rating

26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. Smart TV. Pet-friendly. Sea views. Close to amenities. Dorchester 7.9 miles; Bridport 20.6 miles. (Ref. 1118900)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £1218

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A rocky shoreline with a small beach a stone wall and garden plants at Weymouth Bay Apartment A in Weymouth
1 of 49
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

A lovely two-bedroom, ground-floor apartment resting in Weymouth, Dorset. Near a beach. Close to amenities. Romantic. Ground-floor. Dorchester 7.5 miles; Bridport 20.5 miles. (Ref. 1083146)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine


for 7 nights From £672

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A living room with a sofa and cushions at Admirals Rest in Weymouth
New property
1 of 8
5
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

  • Sykes rating

Admirals Rest is a pleasant apartment in Weymouth, Dorset, featuring open-plan living, off-road parking, and a beach within easy walking distance. Dorchester 7.9 miles; Bridport 21.6 miles. (Ref. 1206605)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly


for 7 nights From £663

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An outdoor area with a table, bottle and glasses at Sea Spray in Bowleaze
1 of 22
5
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.2★

    Good

  • Sykes rating

Sea Spray is a pleasant, open-plan holiday home perched on the edge of Bowleaze, Dorset, enjoying sea views and a short walk to a beach and a pub. Weymouth 2.1 miles; Dorchester 6.8 miles; Yeovil 27.5 miles. (Ref. 1174075)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine


for 7 nights From £529

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The exterior of a white terraced house with blue doors and window sills at South Harbour Cottage in Weymouth
1 of 17
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.4★

    Good

  • Sykes rating

A pretty, renovated terraced cottage, close to the old harbour and Brewers Quay in Weymouth. WiFi. Pet-friendly. Close to beach. Dorchester 8.4 miles; Bridport 19.2 miles. (Ref. 1043009)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £574

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A living room with a blue sofa and television at Saddlers Cottage in Weymouth
Offer
1 of 17
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6★

    Outstanding

  • Sykes rating

A well-positioned, two-bedroom home resting in Weymouth, Dorset. Close to amenities, attractions and beach. Pet-friendly. Near AONB. Enclosed small courtyard. Dorchester 7.5 miles; Bridport 19.2 miles. (Ref. 1132007)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

  • £63 off - Sat 24th Oct to 31st Oct 2026


for 7 nights From £412

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A living room with a blue sofa and ottoman near a fireplace and television at Owls Rest in Weymouth
1 of 36
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6★

    Outstanding

  • Sykes rating

A homely, mid-terrace cottage based in Weymouth. Enclosed decking. Smart TV. Beach nearby. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1094925)

  • Pets go free
  • Wi-fi
  • Baby-friendly


for 7 nights From £502

Last booked yesterday
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A beachfront with kayaks lined up near houses and water at Fairways in Wyke Regis
1 of 22
5
Wyke Regis, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.4★

    Good

  • Sykes rating

Fairways is a delightful house situated less than 2 mins walk to Smallmouth beach in Wyke Regis, Dorset, boasting an enclosed garden, Smart TV, and private driveway parking. Weymouth 2.5 miles; Dorchester 10.2 miles; Poole 34.1 miles. (Ref. 1047698)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £622

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A harbor with boats docked near buildings and a raised drawbridge at Harbours Edge in Brewers Quay Harbour
1 of 27
5
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.2★

    Good

  • Sykes rating

Perfectly located on the harbour side in the heart of Weymouth. Watch the boats sail by and the daily catch being landed. (Ref. 994172)

  • Wi-fi
  • Washing machine


for 7 nights From £471

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A house with stone and wooden exterior at Everdene Upwey near Weymouth
1 of 46
5
Upwey near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.7★

    Outstanding

  • Sykes rating

A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. En-suite, modern features. Shop and pub within walking distance. Weymouth 3.5 miles. (Ref. 932160)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £673

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A multi-story brick house with bay windows and greenery in front at The Lobster Pot in Weymouth
1 of 28
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6★

    Outstanding

  • Sykes rating

The Lobster Pot, a nicely-presented apartment rests in the gorgeous seaside town of Weymouth in Dorset. Open plan. En-suite. Close to beach and amenities. Dorchester 8.7 miles; Bridport 20.4 miles. (Ref. 1151706)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights From £428

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