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Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 347 cottages

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  • Sleeps8
  • Bedrooms4
  • PetsNo
  • Sykes rating

Sunningdale Rise is a striking, detached home on a gated development with off-road parking, close to a beach, in the village of Preston in Dorset. Weymouth 2.5 miles. (Ref. 1149947)

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

7 nights from $1845

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.1

    Good

  • Sykes rating

Tranquil Tides is a well-positioned, ground-floor apartment resting in Weymouth, Dorset. Romantic. Near the beach and amenities. Enclosed courtyard. Pet friendly. Central. Dorchester 7.7 miles; Bridport 20.3 miles. (Ref. 1132772)

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

7 nights from $657

Travel plans can change

Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).

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  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

Mellstock is a charming property resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Shared garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105443)

  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly

7 nights from $723

  • Sleeps4
  • Bedrooms2
  • PetsNo

    3.9

    Good

  • Sykes rating

A well-presented apartment with views over Portland Marina in Castletown, Dorset. Balcony. En-suite. Beach nearby. Portland 2.1 miles; Weymouth 5 miles. (Ref. 1136982)

  • Wi-fi
  • Washing machine

7 nights from $639

  • Sleeps5
  • Bedrooms3
  • PetsYes
  • Sykes rating

Vinney Cottage is a traditional, farm-style thatched home in Owermoigne near Broadmayne, Dorset, with ground-floor living and a pet-friendly policy. Dorchester 6.8 miles; Puddletown 7.6 miles; Weymouth 8.6 miles. (Ref. 1164354)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine

7 nights from $805

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.2

    Good

  • Sykes rating

The Cottage is a charming, two-bedroom townhouse resting in Weymouth, Dorset. Close to amenities. Smart TV. Enclosed balcony. Dorchester 8.5 miles; Bridport 20.6 miles. (Ref. 1137088)

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

7 nights from $751

  • Sleeps4
  • Bedrooms3
  • PetsYes

    3.4

  • Sykes rating

Chapelhay Cottage is a lovely, terraced cottage nestled into the seaside town of Weymouth, Dorset. Close shop and a pub. Close to a beach. Jurassic Coast. Portland 5.9 miles; Dorchester 8.4 miles; Lyme Regis 28.3 miles. (Ref. 1131030)

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

7 nights from $801

Last booked yesterday
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Travel plans can change

Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).

Find out more. T&Cs apply

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A gorgeous cottage nestled in the picturesque village of Upwey in Dorset. Woodburning stove. Family-friendly. Smart TV. Dorchester 4 miles; Weymouth 4.8 miles. (Ref. 1072671)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from $546

  • Sleeps6
  • Bedrooms3
  • PetsNo

    3.6

    Good

  • Sykes rating

A lovely three-bedroom cottage perched in Easton, Dorset. Smart TV. Near a beach. Electric fire. Close to amenities. Enclosed garden. Weymouth 7 miles. (Ref. 1122341)

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

7 nights from $859

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2

    Good

  • Sykes rating

A characterful, thatched cottage resting in Langton Herring near Chickerell, Dorset. Original features. Close to amenities. Dorset AONB. Pet-friendly. Abbotsbury 4.5 miles; Weymouth 5.8 miles; Portland 9.3 miles; Dorchester 9.7 miles. (Ref. 1123272)

  • Wi-fi
  • Baby-friendly

7 nights from $729

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

Emminster is a lovely abode resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Shared garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105445)

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

7 nights from $773

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Monaloe, a lovely three-bedroom house is located in beautiful seaside resort town of Weymouth, Dorset. Pet friendly. Close to beach and amenities. On the Jurassic Coast. Isle of Portland 5.6 miles; Dorchester 8.2 miles. (Ref. 1059916)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $788

  • Sleeps5
  • Bedrooms3
  • PetsYes

    3.6

    Good

  • Sykes rating

Neptune cottage situated in the Isle of Portland is very cosy and comfortable. Perfect for dog walks. Beach 2 min. Welcomes two dogs. Pub 5 min, shop 10 min. Weymouth 5 miles. (Ref. 994425)

  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from $738

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.3

    Good

  • Sykes rating

A lovely, second-floor apartment resting in Portland. Sea views. Pet free. Studio-style. Fortuneswell 2.7 miles; Weymouth 7.7 miles; Dorchester 15.3 miles; West Bay 22.9 miles. (Ref. 1099649)

  • Wi-fi
  • Off-road parking

7 nights from $436

Travel plans can change

Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).

Find out more. T&Cs apply

  • Sleeps8
  • Bedrooms5
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Victorian Town House is a large, coastal property resting in the seaside town of Weymouth, Dorset. Close to a shop, a pub, and a beach. Large property. Dorchester 7.5 miles; West Bay 17.5 miles. (Ref. 1035186)

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

7 nights from $874

  • Sleeps4
  • Bedrooms3
  • PetsNo

    4.1

    Good

  • Sykes rating

A wonderful holiday home resting on the outskirts of Portesham, Dorset. Countryside views. Open-plan living. Barbecue. Decking. Weymouth 8 miles; Dorchester 8 miles. (Ref. 1127855)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom

7 nights from $529

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Chenies is a traditional cottage in the delightful hamlet of Osmington Mills near Preston, Dorset. Sea views. Near a pub. Characterful. Open fire. Preston 2.8 miles; Weymouth 5.9 miles. (Ref. 1149628)

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

7 nights from $740

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.4

    Good

  • Sykes rating

Sunny Croft is a delightful 1930s bungalow in Broadmayne, near Dorchester, Dorset. Stunning countryside views. Hot tub. Large garden. Private parking. Dorchester 4 miles; Weymouth 7.5 miles. (Ref. 977681)

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

7 nights from $1032

  • Sleeps4
  • Bedrooms2
  • PetsNo

    3.9

    Good

  • Sykes rating

Harbour Retreat is a delightful three-storey cottage by the harbourside in Brewers Quay Weymouth, Dorset. Close to beach, shops and amenities. Dishwasher. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1139963)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $800

  • Sleeps10
  • Bedrooms5
  • PetsNo

    4.2

    Good

  • Sykes rating

Sleeps 10, fully renovated 5 storey Georgian sea front house, Large TV, sea views, 3 en-suite bedrooms, less than 50m to the beach. WiFi. (Ref. 1001820)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from $1990