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Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 344 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A lodge sleeping four people, Bowleaze area of Weymouth. Dog friendly. Large garden. Parking for two cars. (Ref. 994500)

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

7 nights from £783

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A contemporary, three-storey property resting by the harbour in Weymouth, Dorset. Gas Fire in Lounge, WiFi. Close to beach and amenities. Weymouth 1 mile; Dorchester 8.6 miles. (Ref. 1058500)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £698

Last booked 2 days ago
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  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.4

    Good

  • Sykes rating

Beautiful holiday cottage over three floors beside Old Harbour in Weymouth. Harbour views. Patio with furniture. Pubs and shop 5 mins. Beach 10 mins. Bridport 22 miles. (Ref. 994256)

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

7 nights from £1234

  • Sleeps9
  • Bedrooms5
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A charming cottage situated on a working farm within the hamlet of Rodden near Abbotsbury. Outstanding scenery. Woodburning stove. Weymouth 7.4 miles; Dorchester 9.4 miles; West Bay 11.7miles. (Ref. 1050484)

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

7 nights from £1030

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A quaint stone-built cottage resting on the outskirts of Weymouth. Open-plan living. Off-road parking. WiFi. Dorchester 6.4 miles; Fortuneswell 8.2 miles. (Ref. 1061544)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Washing machine

7 nights from £534

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic Coast. Amazing views. Shared access to lighthouse observatory. Shared use of seasonal outdoor heated pool and Jacuzzi. (Ref. 12494)

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

7 nights from £710

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • 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)

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

7 nights from £874

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A contemporary townhouse situated just a stone’s throw from Chesil Beach. Pet-friendly. Three floors. Beach views. Weymouth 4.5 miles. (Ref. 1084822)

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

7 nights from £561

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. En-suite master. Lake view. Pet-friendly. Dorchester 7.8 miles; Bridport 18.6 miles. (Ref. 1153879)

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

7 nights from £801

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A stylish and contemporary apartment overlooking Weymouth Harbour in Dorset. Balcony. Underfloor heating. Smart TV. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059265)

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

7 nights from £666

Last booked 3 days ago
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

This wonderful renovated cottage is situated in the village of Abbotsbury, near the coastal town of Weymouth, Dorset. Rustic, cosy interior. stove, Weymouth 8.8 miles. (Ref. 992021)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £593

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Contemporary barn conversion, close to the Dorset coast. Secluded garden. Solid oak flooring. Five minute drive to Weymouth. (Ref. 994207)

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

7 nights from £687

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

This fabulous three-bedroom abode resides in Weymouth, Dorset. Sea glimpses. Smart TV. Open-plan. Near an AONB. Dorchester 7 miles; Bridport 19.5 miles. (Ref. 1125198)

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

7 nights from £679

Last booked 2 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

One @ No36 is a delightful duplex apartment with the beach on your doorstep, with the convenience of off-road parking, in Weymouth, Dorset. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162201)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £712

  • 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 £537

Last booked yesterday
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  • 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 £567

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A beautiful terraced fisherman’s cottage resting in the coastal town of Weymouth, Dorset. Close to a beach. Close to a pub. TV. Dorchester 8.4 miles; West Bay 18.1 miles, Lyme Regis 32.6 miles. (Ref. 1133009)

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

7 nights from £568

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

This cottage boast style, character, and a fabulously contemporary interior. Central location. Surrounded by history. WiFi. Rodwell 0.9 miles. (Ref. 1005313)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £650

  • Sleeps6
  • Bedrooms3
  • PetsYes

    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)

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

7 nights from £762

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A charming reverse-level cottage in the village of Upwey, Dorset. Close to amenities. Woodburning stove. In an Area of Outstanding Natural Beauty. Romantic. Walkers & Cyclists. Weymouth 4.5 miles; Dorchester 4.6 miles. (Ref. 1072756)

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

7 nights from £805