Chiswell On Portland Holiday Cottages

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

  • Sleeps7
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

First floor comfortable apartment sleeping up to 7 people close to the beach in Weymouth. Welcomes two dogs. Shared garden. Beach 2 min. Shop 10 min. Pub 5 min. Dorchester 7.6 miles. (Ref. 994772)

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


for 7 nights From £648

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. Pet-friendly. WiFi. Enclosed garden. (Ref. 1008404)

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


for 7 nights From £555

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    4.5

    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)

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


for 7 nights From £998

  • 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

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

3 Compass Point is a stylish, ground-floor apartment resting in Weymouth, Dorset. Near beach and amenities. Contemporary. Open-plan. Private parking. Dorchester 6.7 miles; Bridport 20.5 miles. (Ref. 1129014)

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


for 7 nights From £663

Last booked yesterday
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  • 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 £474

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. On-site facilities. Family-friendly. Lakeside views. Woodburning stove. Puddletown 5.3 miles; Dorchester 5.6 miles; Weymouth 10 miles. (Ref. 1138508)

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


for 7 nights From £810

  • 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

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

Delightful terraced cottage. Central Weymouth location. Close to Harbour and beach . sleeping 4. Enclosed garden. WiFi. Weymouth beach just 10 minutes away. (Ref. 998253)

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


for 7 nights From £617

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

A wonderful three-storey holiday cottage settled in the seaside resort of Weymouth in Dorset. Washing machine. Enclosed garden. Close to the beach. Dorchester 7.7 miles; Bridport 19.9 miles. (Ref. 1096129)

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


for 7 nights From £708

  • Sleeps5
  • Bedrooms2
  • Pet FriendlyNo

    4.6

    Outstanding

  • Sykes rating

Directly on the seafront. First floor period apartment. Bright and comfortable. Breath-taking sea views. En-suite shower room. WiFi. Off road parking with garage. (Ref. 993989)

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


for 7 nights From £673

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.3

    Good

  • 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


for 7 nights From £508

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

This picturesque cottage, situated in the village of Upwey, with parking. Short drive to Weymouth. Close to pub and tea rooms. Lovely walks nearby. (Ref. 994658)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights From £485

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

Beautiful apartment, that welcomes one well behaved dog, located on the esplanade, perfect for discovering the delights of Weymouth. With wifi and off-road parking for two small to mediums sized cars. (Ref. 1197674)

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


for 7 nights From £836

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6

    Outstanding

  • Sykes rating

Traditional Portland Cottage. Beautiful scenery walks. Close to pubs. (Ref. 993922)

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


for 7 nights From £529

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.4

    Good

  • Sykes rating

Anchor Cottage is a traditional 19th-century Portland Stone cottage resting in the charming village of Weston, Portland, Dorset, with off-road parking. Fortuneswell 1.6 miles; Weymouth 7 miles; Dorchester 14.1 miles; West Bay 21.8 miles. (Ref. 1160217)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights From £504

Last booked yesterday
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