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Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 359 cottages

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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Three bedrooms on Portland, moments from Chesil beach. Balcony overlooking sea and coastline. (Ref. 994701)

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

7 nights from €701

  • Sleeps7
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A well-positioned, three-storey home resting in Fortuneswell, Dorset. Sea views. Close to amenities and the beach. Family-friendly. Private decked area. Near AONB. Weymouth 5.3 miles. (Ref. 1120221)

  • Wi-fi
  • Off-road parking

7 nights from €728

Last booked yesterday
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  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Detached, large and modern house for large group of friends or big family. WiFi. Garden with enclosed patio. Parking for 2 cars. Shop and pub 10 min. Beach 5 min. Weymouth 5 miles. (Ref. 994499)

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

7 nights from €810

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.3

    Good

  • Sykes rating

The Old Portland Courthouse is spacious, comfortable luxury holiday home. Sleeps 8 people. Wifi. Pub and shop 10 min. Beach 5 min. Weymouth 5 miles. (Ref. 994487)

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

7 nights from €1337

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A well-presented, upper-ground floor apartment set in a contemporary development in Weymouth, Dorset. Beach nearby. Adults only. Smart TV. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1123114)

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

7 nights from €700

Last booked 2 days ago
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  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8

    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)

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

7 nights from €1130

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4

    Good

  • Sykes rating

Pretty cottage in the heart of Weymouth. Harbour views. Near to local amenities and town centre. Close to Weymouth Beach. WiFi. Pets welcome. Dorchester 8.5 miles. (Ref. 994047)

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

7 nights from €810

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

Grade II listed house just a few moments walk from Weymouth Beach, Ideally located in the heart of old Weymouth. 5 minutes walk to shops, bars and restaurants. Off Road Parking. (Ref. 994168)

  • Wi-fi
  • Washing machine

7 nights from €494

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A delightful, mid-terrace home just moments from the beach in the village of Wyke Regis, Weymouth. Pet-friendly. WiFi. Off-road parking for one car. Weymouth 2.6 miles; Dorchester 10.2 miles. (Ref. 1071852)

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

7 nights from €717

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A well-presented, ground-floor apartment in Weymouth, Dorset. Open-plan. Close to beach. Near an AONB. Ground-floor living. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1126298)

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

7 nights from €529

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Centrally located in Weymouth beautiful holiday home for family or friends. Walking distance to town centre. WiFi. Shop and pub 5 min. Beach 10 min. Dorchester 8.5 miles. (Ref. 994461)

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

7 nights from €701

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A contemporary second-floor apartment resting on the Weymouth Seafront, 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 €659

Last booked yesterday
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Modern family house located on the edge of Weymouth, with sea views. Short drive to town centre. Welcomes two dogs. Garden. Pub and shop 10 min. Beach 2 min. Bridport 19 miles. (Ref. 994759)

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

7 nights from €706

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.3

    Good

  • Sykes rating

Exceptional harbourside cottage located in the heart of Weymouth, Dorset. WiFi. Off-road parking. Harbour and sea views. Shop 0.1 miles, pub 0.3 miles. (Ref. 1000215)

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

7 nights from €1280

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Situated in a gated complex near Weymouth harbour. WiFi. Parking. Close to bars and restaurants. (Ref. 994560)

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

7 nights from €648

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Modern and beautiful cottage in the heart of Weymouth. Close to town centre. Wifi. Parking for two cars. Landscaped garden with patio. Shop and pub 5 min. Bridport 22.5 miles. (Ref. 994369)

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

7 nights from €632

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Quay cottage is a period terraced property in Weymouth. Short walk to town centre. Close to Old Harbour. WiFi. Pub and shop 5 min. Beach 10 min. Dorchester 8.5 miles. (Ref. 994576)

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

7 nights from €664

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Sleeping 4 cosy cottage in Weymouth. Close to harbour and all amenities. Gated development. (Ref. 994605)

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

7 nights from €664

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Beautiful 1 bedroom stable conversion in the heart of the harbour area in Weymouth. WIFI, Close to town centre and beach. Parking for one car. (Ref. 1096825)

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

7 nights from €556

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Dirdale is a tasteful lodge resting in rural 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. 1105458)

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

7 nights from €768

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