Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 363 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
The exterior of a brick house with a tiled roof a black door a paved path and plants at Badbury Lodge Brewers Quay Harbour
26
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights From $711

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A three-story red brick residential building with multiple white-framed windows and black doors at Admiral's Quarter Apartment 5 in Weymouth
11
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6★

    Outstanding

  • Sykes rating

A well-presented, ground-floor apartment in Weymouth, Dorset. Open-plan. Close to beach. Near an AONB. Ground-floor living. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1126298)

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


for 7 nights From $619

Last booked 2 days ago
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Two adjacent houses with black front doors and small porches with awnings and shrubs outside at Anvil House in Brewers Quay Harbour
25
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

A pretty little modern house just a few minutes walk from the harbourside and local amenities. Close to the South West Coast Path. (Ref. 993929)

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


for 7 nights From $767

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A stone thatched roof cottage with white framed windows and a porch along a quiet street at Cobblers Cottage in Langton Herring
44
Langton Herring, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

Cobblers Cottage is a traditional stone built thatched cottage in the quiet Dorset village of Langton Herring, close to the Jurassic coast. Abbotsbury 5 miles; Weymouth 5.5 miles; Portland 9.4 miles; Dorchester 9.9 miles. (Ref. 1171904)

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


for 7 nights From $669

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Three modern two story houses with green window frames and stone wall facades with a paved driveway and some plants at Pebbles Reach in Fortuneswell
42
Fortuneswell, Dorset, DT5
  • Sleeps7
  • Bedrooms3
  • Pet FriendlyYes

    4.6★

    Outstanding

  • Sykes rating

An attractive, terraced, three-storey house near Chesil Beach in Fortuneswell, Dorset. Off-road parking. Dog-friendly. Enclosed terrace. Smart TV. Bedroom with en-suite. Weymouth 4.6 miles. (Ref. 1091335)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From $944

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A red brick building with multiple windows and a sign on Trinity Road at Monarch Brewers Quay Harbour
36
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

A delightful, romantic bolthole in the third-floor in Weymouth, Dorset. Balconies. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1078324)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From $741

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A semi detached house with a driveway and a garage at Lagoon View in Wyke
33
Wyke, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

A charming cottage based in the village of Wyke Regis, Dorset. Beach nearby. Dishwasher. Electric fire. Wifi. Weymouth 2.1 miles; Dorchester 9.7 miles. (Ref. 1121449)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From $857

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A row of multi-colored buildings along a waterfront with a boat named Top Cat III docked at Safe Harbour Brewers Quay harbour
38
Brewers Quay harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

Cosy, comfortable and luxurious three storey house in Weymouth. Perfect for families. WiFi. Courtyard. One dog welcome. Pub and shop 5 min. Beach 10 min. Dorchester 8 miles. (Ref. 994606)

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


for 7 nights From $1357

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A brick building with multiple bay windows and doors along a street at The BoBo House in Weymouth
56
Weymouth, Dorset, DT4
  • Sleeps12
  • Bedrooms6
  • Pet FriendlyNo

    5.0★

    Perfect

  • Sykes rating

The BoBo House is a delightful terraced holiday home resting in the popular coastal town of Weymouth in Dorset set over four floors and near the beach. Dorchester 7 miles; Bridport 17 miles. (Ref. 1059621)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Games room


for 7 nights From $1373

Last booked 3 hours ago
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An outdoor balcony with a table set with plates cups a teapot and pastries with buildings in the background at Spindrift Brewers Quay Harbour
38
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms4
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

Spindrift is a characterful, home resting upon Brewers Quay Harbour in Dorset. Original features. Close to amenities, attractions and the harbour. Balcony. Dorchester 8.5 miles; West Lulworth 15.3 miles. (Ref. 1137640)

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


for 7 nights From $874

Last booked yesterday
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Front view of three terraced houses with plants and bushes in front at Kingfisher Cottage in Weymouth
19
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

A terrace property resting close to the beach and harbour in Weymouth. Allocated parking for two cars. WiFi. Fortuneswell 4.7 miles; Dorchester 8.9 miles. (Ref. 1038344)

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


for 7 nights From $645

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A corner of a living room with a bay window showing a view outside and a TV on a white cabinet at Waterside in Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

Stylish renovated ground floor apartment in Weymouth. Town centre a short walk away. WiFi. Welcomes one dog. Pub and shop 5 min. Beach 10 min. Dorchester 8.3 miles. (Ref. 994763)

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


for 7 nights From $894

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Front exterior of a house with a black door two potted plants and pink flowers in a garden at 6 The Terrace Brewers Quay Harbour
42
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. Quality finish. Sea and harbour views. Enclosed garden. Raised elevation. Dorchester 8.5 miles; West Lulworth 15.5 miles. (Ref. 1096352)

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


for 7 nights From $1202

Last booked 3 hours ago
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Quay Cottage - 994576 - photo 1
28
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

Quay cottage is a period terraced property in Weymouth. Short walk to town centre. Close to Old Harbour. WiFi. Pub and shop 5 min. Beach 10 min. Dorchester 8.5 miles. (Ref. 994576)

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


for 7 nights From $806

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A detached house with a double garage and driveway at Connaught Gardens in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

Large, modern house nestled on the outskirts of Weymouth, 1 mile from the beach and restaurants. Off-road parking. WiFi. Enclosed garden. (Ref. 1001446)

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


for 7 nights From $1046

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A house with garage and driveway at The Chocolate Box in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

A lovely three-storey house resting in Weymouth, Dorset. Dog-friendly. Near a beach. Off-road parking. Private garden. Dorchester 8.7 miles; Bridport 19.1 miles. (Ref. 1092302)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From $1147

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A small outdoor seating area with chairs and a table surrounded by flowers in front of a brick house with blue shutters at Garibaldi Cottage in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

Garibaldi Cottage is a lovely, coastal home resting in the town of Weymouth in Dorset, enjoying close proximity to a nearby shop, beach, and pub. Dorchester 8.2 miles; Bridport 20.1 miles. (Ref. 1156408)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights From $733

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A brick terraced house with a white front door gravel front garden and small plants at Home Waters in Wyke Regis
23
Wyke Regis, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

Off road parking. Sleeping 6 close to Portland marina. Dog friendly. (Ref. 994270)

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


for 7 nights From $803

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A house facade with windows and doors at 8 Park View Grove Weymouth
40
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms3
  • Pet FriendlyYes

    5.0★

    Perfect

  • Sykes rating

Park View is a welcoming house in Weymouth, Dorset, offering three bedrooms, enclosed rear garden, and easy reach of shop, pub, and beach. Dorchester 8.4 miles; Bridport 19 miles; Charmouth 25.5 miles. (Ref. 1198402)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights From $838

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A living room with a sofa and dining area at Betty's Buoy Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    5.0★

    Perfect

  • Sykes rating

Betty’s Buoy is a stylish first-floor apartment in Weymouth, Dorset, with open-plan living and easy access to the beach. Dorchester 7.5 miles; Bridport 18.8 miles. (Ref. 1168986)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From $602

Last booked 8 hours ago
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