Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 344 cottages

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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.2

    Good

  • Sykes rating

Situated in the beautiful Bowleaze Cove area of Weymouth, just seconds from a beach is this enchanting holiday home. (Ref. 994020)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Sat 14th Jun to 5th Jul 2025

  • 10% off - Sat 12th Jul to 26th Jul 2025

7 nights from €991

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.4

    Good

  • Sykes rating

Overlooking the beautiful Nothe Gardens and, through the trees, the coastal views of Weymouth Bay and Portland Harbour is Harbour View Bungalow. (Ref. 994244)

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

7 nights from €1268

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Bright contemporary property perfect groups of guests in the Isle of Portland. Sea views. WiFi. Shop 10 min. Pub 5 min. Beach 5 min. Weymouth 4.9 miles. (Ref. 994754)

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

7 nights from €900

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo
  • Sykes rating

A historic, 18th-century cottage resting in Portland, Dorset. Sea views. Character features. Hot tub. Near a pub. Easton 1.5 miles; Chiswell 3 miles; Weymouth 8 miles. (Ref. 1122551)

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

7 nights from €899

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.0

    Good

  • Sykes rating

Close to the harbour in Weymouth, Semi detached house, access to South West Coast path, WIFI, Close to shops, restaurants and café’s, suitable for families. (Ref. 994639)

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

7 nights from €848

  • 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

7 nights from €734

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.3

    Good

  • Sykes rating

Lovely and comfortable cottage next to the harbour in Weymouth. Wifi. Shop and pub 5 min. Beach 1 mile. Dorchester 8 miles. (Ref. 994351)

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

7 nights from €683

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

Modern 3 Storey house. Close to the Harbour, Newton’s Cove and Brewers Quay. WIFI. Parking for one car. 5 minutes to local shop. 15 minute walk to town centre. (Ref. 993939)

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

7 nights from €899

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.2

    Good

  • Sykes rating

Sleeps six in Weymouth, patio garden. Off road parking. 10 mins walk from Weymouth harbour. (Ref. 994586)

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

7 nights from €753

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.4

    Good

  • Sykes rating

Modern and well-furnished Hops House is an ideal family holiday home in Weymouth. WiFi. Pub and shop 5 min. Beach 1 mile. Dorchester 9 miles. (Ref. 994277)

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

7 nights from €900

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Easter Weekend open to book! A characterful first-floor apartment set on the Dorset coast, within the town of Weymouth. Outstanding sea views. Central location. Family-friendly. Isle of Portland 7 miles; Dorchester 7.2 miles; West Bay 18.1 miles. (Ref. 1049890)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Fri 13th Jun to 31st Jul 2025

7 nights from €1072

  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Sunset Lodge is a lovely retreat on Portland, moments from Chesil beach in Fortuneswell, Dorset, enjoying wonderful coastal views from the a balcony. Weymouth 5.3 miles. (Ref. 1173296)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from €733

  • 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 €663

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Winkle Cottage is a wonderful holiday home, set over three floors, situated in the popular coastal town of Weymouth in Dorset by the historic harbour. Dorchester 8.5 miles; Bridport 19.3 miles. (Ref. 1140944)

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

7 nights from €719

  • Sleeps6
  • Bedrooms3
  • PetsNo
  • Sykes rating

Farthings is a homely, semi-detached holiday cottage located along the coast in Weymouth, Dorset, with off-road parking and a short walk to a beach. Dorchester 7.6 miles; Bridport 19.7 miles. (Ref. 1174458)

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

7 nights from €792

Last booked 1 hour ago
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  • Sleeps6
  • Bedrooms4
  • PetsYes

    4.4

    Good

  • Sykes rating

Lovely 4 bedroom house in gated area. Close to Weymouth harbour. Secure gated parking for one car. Welcomes two dogs. WiFi. (Ref. 994213)

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

7 nights from €958

  • Sleeps6
  • Bedrooms4
  • PetsYes
  • Sykes rating

Amy Cottage is a beautiful thatched cottage with a toasty gas fire and accepting pets, located in Dorset's West Lulworth on the Jurassic coastline. Wareham 8.7 miles; Weymouth 14.6 miles. (Ref. 1166887)

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

7 nights from €1010

  • Sleeps10
  • Bedrooms5
  • PetsNo

    4.2

    Good

  • Sykes rating

Sleeps 10, fully renovated 5 storey Georgian sea front house, Large TV, sea views, 3 en-suite bedrooms, less than 50m to the beach. WiFi. (Ref. 1001820)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from €1824

  • Sleeps10
  • Bedrooms5
  • PetsNo

    4.3

    Good

  • Sykes rating

Beautiful, Georgian seafront house, nestled in the lively town of Weymouth. Sea views. En-suite bedrooms. WiFi. Beach less than 50 metres away. (Ref. 1006583)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from €1759

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A Grade II listed, maisonette apartment in the Dorset town of Weymouth. WiFi. One dog welcome. Pub and shop within 0.1 miles. (Ref. 1011525)

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

7 nights from €912

Last booked yesterday
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