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Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 348 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

123 On The Sea is a lovely, two-bedroom apartment residing in Weymouth, Dorset. Near Dorset AONB. Sea views. Close to amenities and a beach. Private balcony. Off road parking. Dorchester 7.3 miles; Bridport 18.9 miles. (Ref. 1133961)

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

7 nights from €639

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

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Beautiful seafront apartment within the popular resort of Weymouth in Dorset. Incredible sea views. WiFi. Centre of Weymouth. (Ref. 1003083)

  • Wi-fi
  • Dishwasher

7 nights from €587

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Charming detached Grade II listed lighthouse cottage at Portland Bill on Dorset's Jurassic Coast. Upside down accommodation with sensational sea views. Shared access to Lighthouse observatory. Shared use of heated pool and Jacuzzi. (Ref. 12497)

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

7 nights from €801

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Wonderfully positioned townhouse just moments from Sandsfoot beach and the South West Coast path. Sea views. Sleeps 6. Off road parking (Ref. 1059103)

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

7 nights from €954

  • Sleeps6
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Bayview Villa is a four-storey townhouse situated in the village of Fortuneswell, Portland. Woodburning stove. Beach views. Courtyard garden. Pet friendly. Near amenities. Weymouth 7.2 miles. (Ref. 1135439)

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

7 nights from €875

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

An enchanting refurbished cottage in the centre of the lovely village of Sutton Poyntz. Fully furnished and comfortable. Sunny patio garden. WiFi. Weymouth 4 miles. (Ref. 994009)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €543

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Norden Cottage is a fine, three-bedroom abode resting in Osmington, Dorset. Woodburning stove. Pet-friendly. Enclosed garden. Close to amenities. Weymouth 4.9 miles. (Ref. 1149647)

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

7 nights from €840

  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

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

7 nights from €657

  • 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 €696

Last booked yesterday
See more details
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    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)

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

7 nights from €776

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

The Corner House is a delightful terrace home resting in the popular seaside town of Weymouth, Dorset. Close to amenities. Near beach. Enclosed courtyard. Dorchester 7.1 miles; Bridport 19.1 miles. (Ref. 1129331)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €656

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

An immaculate second-floor apartment resting in the centre of Weymouth. Marina views. Open-plan living room. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059264)

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

7 nights from €780

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A pretty village lodge, close to the seaside town of Weymouth in Dorset. Traditional. Beautiful Mediterranean-style garden. WiFi. Dorset AONB. Dorchester 4.9 miles. (Ref. 1017591)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Sat 12th Apr to 26th Apr 2025

  • 10% off - Sat 24th May to 31st May 2025

7 nights from €460

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Large kitchen diner. Beautiful rural location. Short walk to the sea. Wi-Fi. In the heart of the Jurassic coastline. Picture postcard thatched cottage. (Ref. 994553)

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

7 nights from €1108

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. Accepts one dog. Pub and shop 5 min. Beach 5 min. Bridport 23 miles. (Ref. 994321)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Sat 31st May to 14th Jun 2025

7 nights from €547

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    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

7 nights from €657

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A stunning holiday home in the bustling seaside town centre of Weymouth in Dorset. Enclosed patio. Near beach. Smart TV. Isle of Portland 6.7 miles; Dorchester 8 miles; Bridport 20.2 miles. (Ref. 1054948)

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

7 nights from €647

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A beautiful and contemporary first-floor apartment overlooking the harbour in Weymouth, Dorset. Balcony with harbour views. Master with en-suite. Allocated parking space. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059263)

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

7 nights from €810

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

This beautiful three-bedroom property resides in West Lulworth, Dorset. Off-road parking. In an AONB. En-suite bedrooms. Close to amenities and a beach. Wareham 8.8 miles; Weymouth 15.3 miles. (Ref. 1126738)

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

7 nights from €910

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

An inviting, mid-terrace house perched on the coast in Weymouth, Dorset. Sea views. Off-road parking. Near the beach. Dorchester 10.2 miles; Bridport 18.8 miles. (Ref. 1082718)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from €551