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Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 359 cottages

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  • Sleeps7
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A well-positioned, three-storey home resting in Fortuneswell, Dorset. Sea views. Close to amenities and the beach. Family-friendly. Private decked area. Near AONB. Weymouth 5.3 miles. (Ref. 1120221)

  • Wi-fi
  • Off-road parking

7 nights from £632

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Three bedrooms on Portland, moments from Chesil beach. Balcony overlooking sea and coastline. (Ref. 994701)

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

7 nights from £609

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A well-positioned, fourth-floor apartment resting in Castletown, Dorset. Sea views. Close to amenities and the beach. Contemporary. Designated parking. Private balcony. Portland 1.9 miles; Weymouth 5.2 miles; Dorchester 12.6 miles. (Ref. 1119638)

  • Wi-fi
  • Swimming pool
  • Dishwasher
  • Washing machine

7 nights from £554

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A wonderful, end-terrace house perched on the coast in Wyke Regis, Dorset. Sea views. Electric fire. Weymouth 2.6 miles; Dorchester 10.2 miles. (Ref. 1091445)

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

7 nights from £708

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Lyme View, delightful coastal property resting in Fortuneswell on the Isle of Portland, Dorset. Close to a beach. Garden. Pet friendly. Close to a shop and a pub. Weymouth 5.2 miles; Abbotsbury 11.9 miles; Dorchester 12.8 miles. (Ref. 1135049)

  • Wi-fi
  • Electric vehicle charging
  • Washing machine

7 nights from £493

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Detached, large and modern house for large group of friends or big family. WiFi. Garden with enclosed patio. Parking for 2 cars. Shop and pub 10 min. Beach 5 min. Weymouth 5 miles. (Ref. 994499)

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

7 nights from £693

  • Sleeps8
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A charming terraced property resting in Fortuneswell, Dorset. Sea views. WiFi. Terrace garden. Pet-friendly. Weymouth 5.2 miles. (Ref. 1035417)

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

7 nights from £562

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A delightful 3 storey fishermans cottage that has been beautifully restored in the harbour area of Weymouth. (Ref. 993928)

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

7 nights from £529

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A contemporary first-floor apartment overlooking the coast in Weymouth, Dorset. Open-plan. Sea views. WiFi. Close to amenities. Dorchester 7.4 miles; Bridport 20.2 miles. (Ref. 1097676)

  • Wi-fi

7 nights from £680

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4

    Good

  • Sykes rating

Pretty cottage in the heart of Weymouth. Harbour views. Near to local amenities and town centre. Close to Weymouth Beach. WiFi. Pets welcome. Dorchester 8.5 miles. (Ref. 994047)

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

7 nights from £693

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Sunset View is a perfectly-positioned, fifth-floor apartment residing in Castletown, Dorset. Sea views. Close to amenities and the beach. Private balcony. Portland 2.1 miles; Weymouth 5 miles; Dorchester 12.4 miles. (Ref. 1141111)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from £472

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A wonderful, bright, second-floor apartment lying at the heart of Weymouth, Dorset. Close to beach. Off-road parking. Open-plan living space. Dorchester 7.8 miles; Bridport 18.5 miles. (Ref. 1114499)

  • Wi-fi
  • Dishwasher

7 nights from £498

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.6

    Outstanding

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A modern studio apartment on the seafront on Weymouth, Dorset. Open-plan living. Sea views. Perfect for couples. (Ref. 1003545)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £402

Last booked 7 hours ago
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A fabulous three-bedroom holiday home in Wyke Regis, Dorset. Pet-friendly. Sea views. Close to beach and amenities. Open-plan. Contemporary. Weymouth 2.2 miles; Dorchester 9.6 miles. (Ref. 1103441)

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

7 nights from £763

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A well-presented, upper-ground floor apartment set in a contemporary development in Weymouth, Dorset. Beach nearby. Adults only. Smart TV. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1123114)

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

7 nights from £608

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A stylish property resting in the resort of Weymouth, Dorset. Enclosed garden. Pet free. Beach nearby. Dorchester 10.1 miles; Bridport 18.8 miles. (Ref. 1100742)

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

7 nights from £610

Last booked yesterday
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  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Modern and comfortable holiday house for up to 8 people in the Isle of Portland. Enclosed garden with patio. Pub and shop 5 min. Beach 5 min. Weymouth 5 miles. (Ref. 994310)

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

7 nights from £966

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A contemporary second-floor apartment resting on the Weymouth Seafront, Dorset. Open-plan living. Sea views. Close to amenities and beach. Pet-free. Stylish. Dorchester 7.8 miles; Bridport 20.3 miles. (Ref. 1092706)

  • Wi-fi
  • Dishwasher

7 nights from £573

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.4

    Good

  • Sykes rating

A delightful cottage situated next to Weymouth harbour in Dorset. Harbour Views. Family-friendly. Dorchester 8.4 miles; West Lulworth 15.5 miles. (Ref. 1061726)

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

7 nights from £776

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A delightful, mid-terrace home just moments from the beach in the village of Wyke Regis, Weymouth. Pet-friendly. WiFi. Off-road parking for one car. Weymouth 2.6 miles; Dorchester 10.2 miles. (Ref. 1071852)

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

7 nights from £623

Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.