Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 352 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

A beautiful two-bedroom, ground-floor apartment resting in Weymouth, Dorset. Open-plan. Romantic. Near a beach. Close to amenities. Dorchester 8.4 miles; Bridport 18.5 miles. (Ref. 1108560)

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

7 nights from £449

  • Sleeps6
  • Bedrooms3
  • PetsNo
  • Sykes rating

This delightful townhouse rests in Chiswell On Portland, Dorset. Private parking. Smart TV. Pet-free. Close to beach. Enclosed courtyard. Weymouth 4.7 miles. (Ref. 1107574)

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

7 nights from £555

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. Open-plan living space. Private parking. Close to the coast. Chickerell 3 miles; Dorchester 8.3 miles; Swanage 28.9 miles. (Ref. 1111030)

  • Wi-fi
  • Dishwasher

7 nights from £574

  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

An attractive, terraced, three-storey house near Chesil Beach in Fortuneswell, Dorset. Off-road parking. Dog-friendly. Enclosed terrace. Smart TV. Bedroom with en-suite. Weymouth 4.6 miles. (Ref. 1091335)

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

7 nights from £612

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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.2

    Good

  • Sykes rating

A characterful, thatched cottage sitting in Osmington near Preston, Dorset. Woodburning stove. Original features. Pet-friendly. Weymouth 5.3 miles; Dorset AONB 10.7 miles; Bournemouth 30.3 miles. (Ref. 1104917)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from £732

  • Sleeps7
  • Bedrooms4
  • PetsNo
  • Sykes rating

A spacious, three-storey house settled in Castletown, Portland, Dorset. Private parking. Bedrooms with en-suite. Smart TVs. Enclosed courtyard. Close to amenities and beach. Pet-free. Weymouth 4.8 miles; Dorchester 12.4 miles. (Ref. 1107230)

  • Wi-fi
  • Dishwasher
  • Ground floor bedroom

7 nights from £848

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • 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

7 nights from £652

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

This charming mid-terraced house lies near Weston on the Isle of Portland. Off-road parking. Enclosed garden. Smart TV. Close to beach. Fortuneswell 2.7 miles; Weymouth 8.1 miles; Dorchester 15.4 miles. (Ref. 1099790)

  • Wi-fi
  • Off-road parking
  • Washing machine
  • Sky TV

7 nights from £534

  • Sleeps6
  • Bedrooms3
  • PetsNo
  • Sykes rating

A charming, three-bedroom cottage resting in Weymouth, Dorset. Enclosed garden. Near beach. Close to amenities. Dorchester 8.4 miles; Bridport 18.9 miles. (Ref. 1099795)

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

7 nights from £686

  • Sleeps2
  • Bedrooms1
  • PetsNo
  • Sykes rating

A romantic, ground-floor apartment sitting in Weymouth, Dorset. Open-plan. Close to amenities and beach. WiFi. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1102992)

  • Wi-fi
  • Ground floor bedroom

7 nights from £420

  • Sleeps2
  • Bedrooms1
  • PetsNo
  • Sykes rating

A contemporary second-floor apartment resting in Weymouth, 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 £504

  • Sleeps9
  • Bedrooms4
  • PetsYes
  • Sykes rating

A stunning, detached home resting in Weymouth, Dorset. Enclosed garden. Near beach. Pet-friendly. Dorchester 7 miles; Bridport 19.7 miles; Poole 30.9 miles. (Ref. 1022573)

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

7 nights from £935

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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Excellent

  • Sykes rating

A sea-front two-bedroom apartment fronting Weymouth bay, Dorset. Beautiful views. En-suite bedroom. Woodburning stove. Near beach. Dorchester 7.6 miles; Bridport 21.3 miles; Poole 31.4 miles. (Ref. 1100406)

  • Wi-fi
  • Dishwasher

7 nights from £580

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A lovely two-bedroom, ground-floor apartment resting in Weymouth, Dorset. Near a beach. Close to amenities. Romantic. Ground-floor. Dorchester 7.5 miles; Bridport 20.5 miles. (Ref. 1083146)

  • Wi-fi
  • Off-road parking
  • Washing machine
  • Ground floor bedroom
  • 65% off - Sat 17th Dec to 24th Dec 2022

7 nights from £570

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

A bright and airy lodge resting in Osmington near Preston, Dorset. Open-plan. Close to beach. Pet-friendly. Weymouth 5.4 miles; Poole 23.4 miles; Bournemouth 29.1 miles. (Ref. 1093891)

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

7 nights from £614

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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

St. John’s View is a modern holiday home in the Isle of Portland with sea views. Over lower ground floor and ground floor. Shop, pub, beach 5 min. Weymouth 4.6 miles. (Ref. 994677)

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

7 nights from £519

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • 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 £434

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A delightful, mid-terrace cottage resting in Brewers Quay Harbour, Dorset. Designated parking. Pet-friendly. Enclosed garden. Weymouth 0.6 miles; Dorchester 8.8 miles; West Lulworth 15.7 miles. (Ref. 1084006)

  • Dishwasher

7 nights from £529

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