Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 349 cottages

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  • Sleeps6
  • Bedrooms3
  • PetsNo

    3.5

    Good

  • Sykes rating

Ocean Swell is a lovely cottage for families or friends in Weymouth. Close to the town centre. WiFi. Shop and pub 5 min. Beach 1 mile. Dorchester 8.5 miles. (Ref. 994710)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £526


for 7 nights £587

Holiday Park

  • Sleeps6
  • Bedrooms2
  • PetsYes
  • Sykes rating

39 Green Lands is a lovely pet-friendly caravan in Weymouth, Dorset, boasting onsite facilities and is close to the beach for a day out. Dorchester 9.2 miles; Bridport 17,6 miles. (Ref. 1185302)

  • Wi-fi
  • Swimming pool


for 7 nights £592

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Brewery View is a stylish, first-floor apartment near the beach in Weymouth, Dorset, with an open-plan living space, balcony, and designated parking. Dorchester 8.8 miles; Bridport 19.4 miles. (Ref. 1189426)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £534

  • Sleeps4
  • Bedrooms2
  • PetsNo

    3.4

  • Sykes rating

A contemporary second-floor apartment set within the town of Weymouth, Dorset. Close to the close. Balcony with views. Dorchester 8.4 miles; Bridport 19.2 miles; Bournemouth 37.1 miles. (Ref. 1052595)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £502

  • Sleeps8
  • Bedrooms3
  • PetsNo
  • Sykes rating

The Beach Condo, a quaint duplex apartment over three floors, in the heart of Weymouth in Dorset features stunning sea vistas, and a nearby beach and pub. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1176421)

  • Wi-fi
  • Dishwasher


for 7 nights £949

  • Sleeps4
  • Bedrooms3
  • PetsYes
  • Sykes rating

Park View is a welcoming house in Weymouth, Dorset, offering three bedrooms, enclosed rear garden, and easy reach of shop, pub, and beach. Dorchester 8.4 miles; Bridport 19 miles; Charmouth 25.5 miles. (Ref. 1198402)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights £566

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

Seahorse Cottage, a delightful stone terraced cottage near Old Harbour in Weymouth, Dorset, boasts a garden, a nearby beach and amenities, and allows pets. Dorchester 7 miles. (Ref. 1191297)

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


for 7 nights £516

  • Sleeps5
  • Bedrooms3
  • PetsYes
  • Sykes rating

Vinney Cottage is a Grade II listed traditional, farm-style thatched home in Owermoigne near Broadmayne, Dorset, with ground-floor living and a pet-friendly policy. Dorchester 6.8 miles; Puddletown 7.6 miles; Weymouth 8.6 miles. (Ref. 1164354)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine
  • 10% off - Fri 1st May to 16th Jun 2026


for 7 nights £836

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Tourist Board rating

The Weymouth House is a welcoming holiday home in Weymouth, Dorset, with a private courtyard and parking permit. Dorchester 7.5 miles; Bridport 18.9 miles. (Ref. 1193951)

  • Wi-fi
  • Washing machine


for 7 nights £1820

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Vista Mare 1 is a pleasant apartment located in the heart of Weymouth in Dorset, enjoying close proximity to a beach and pub, as well as a warm welcome to pets. Dorchester 7.5 miles; Bridport 21.1 miles. (Ref. 1164685)

  • Wi-fi
  • Dishwasher


for 7 nights £1360

  • Sleeps4
  • Bedrooms1
  • PetsNo
  • Tourist Board rating

Apartment 1 Brewers Quay is a stylish property in Weymouth’s historic Quayside, boasting modern interiors and allocated parking. Dorchester 8.6 miles; Bridport 19.3 miles. (Ref. 1166031)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £467

Last booked today
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  • Sleeps2
  • Bedrooms1
  • PetsNo

    3.3

  • Sykes rating

Cove Cottage Hideaway is a romantic, terrace abode near the coast in Chiswell on Portland, Dorset. Close to amenities and beach. Sea Views. Romantic. Weymouth 5.2 miles. (Ref. 1150238)

  • Wi-fi


for 7 nights £602

Holiday Park

  • Sleeps5
  • Bedrooms2
  • PetsNo
  • Tourist Board rating

Durdle Door Holiday Park Holiday Accommodation 6617 is a well‑equipped caravan in Wareham, Dorset, with sea views to enjoy and an open‑plan layout. Corfe Castle 12.5 miles; Swanage 17.8 miles; Poole 18.7 miles. (Ref. 1189021)

  • Wi-fi
  • Baby-friendly
  • 5% off - Sun 1st Mar to 30th Apr 2026


for 7 nights £501

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • 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)

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


for 7 nights £829

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Vista Mare 3 is a delightful apartment located in the centre of Weymouth, a vibrant town in Dorset, with lovely sea views from an open-plan living space. Dorchester 7.5 miles; Bridport 21.1 miles. (Ref. 1164688)

  • Wi-fi
  • Dishwasher


for 7 nights £910

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

Harbourside is a charming, dog-friendly, Grade II listed house in Weymouth, Dorset, set over three stories, with open-plan living and a private courtyard. Dorchester 8.8 miles; Bridport 18.9 miles. (Ref. 1172365)

  • Wi-fi
  • Washing machine


for 7 nights £438

Last booked 1 hour ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Wren, a stylish, two-bedroom home rests in Upwey, Dorset. Near AONB. Close to amenities. Near the beach and attractions. Enclosed garden. Contemporary. Weymouth 4.2 miles; Dorchester 4.4 miles. (Ref. 1138702)

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


for 7 nights £514

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

The Old Post Office, a stylish pet-friendly house nestled in the town Weymouth, Dorset, features a Smart TV, proximity to the beach and marina. Dorchester 8.5 miles; Bridport 20.5 miles. (Ref. 1127439)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £517

Last booked yesterday
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