Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 363 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

A stunning holiday home in the bustling seaside town centre of Weymouth in Dorset. Enclosed patio. Near beach. Smart TV. Isle of Portland 6.7 miles; Dorchester 8 miles; Bridport 20.2 miles. (Ref. 1054948)

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


for 7 nights From £558

  • Sleeps7
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £713

Last booked 9 hours ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Harbour Retreat is an eclectic first-floor apartment close to the harbour and beach, with roadside parking, in the heart of Weymouth in Dorset. Dorchester 8.3 miles; Bridport 20.5 miles. (Ref. 1164179)

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


for 7 nights From £508

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    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


for 7 nights From £610

  • Sleeps8
  • Bedrooms3
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

A charming terraced property resting in Fortuneswell, Dorset. Sea views. WiFi. Terrace garden. Pet-friendly. Weymouth 5.2 miles. (Ref. 1035417)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £454

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

Off road parking. Sleeping 6 close to Portland marina. Dog friendly. (Ref. 994270)

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


for 7 nights From £608

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.5

    Outstanding

  • Sykes rating

Ground floor apartment in Weymouth, sleeps 4, wifi, allocated parking, close to the beach, shops and marina. Open plan living kitchen diner. (Ref. 1091449)

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


for 7 nights From £536

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.5

    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


for 7 nights From £610

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

Cedar Drive is a charming house in Preston, Dorset, boasting ground-floor living, close proximity to local amenities and the coast for great days out. Weymouth 3.6 miles (Ref. 1173784)

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


for 7 nights From £519

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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


for 7 nights From £461

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Cobblers Cottage is a traditional stone built thatched cottage in the quiet Dorset village of Langton Herring, close to the Jurassic coast. Abbotsbury 5 miles; Weymouth 5.5 miles; Portland 9.4 miles; Dorchester 9.9 miles. (Ref. 1171904)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £480

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Cosy, comfortable and luxurious three storey house in Weymouth. Perfect for families. WiFi. Courtyard. One dog welcome. Pub and shop 5 min. Beach 10 min. Dorchester 8 miles. (Ref. 994606)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £1010

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7

    Outstanding

  • Sykes rating

A well-positioned, three-storey property resting in Weymouth, Dorset. Sea views. Close to amenities and the beach. Enclosed garden. Elevated position. Dorchester 8.9 miles; Bridport 20.6 miles. (Ref. 1118939)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £647

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Coastguard View is a lovely holiday cottage resting near the coast in Portland Bill on the Isle of Portland, Dorset with a Smart TV and open-plan space. Easton 2.6 miles; Fortuneswell 3.6 miles; Weymouth 9.1 miles. (Ref. 1169819)

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


for 7 nights From £600

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Upper ground floor apartment in the Admiral’s Quarter development. Partial sea views from the full length windows in the sitting rooms. Modern furnishings. Perfect for a family holiday exploring the delights of Weymouth. Wifi. (Ref. 994438)

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


for 7 nights From £501

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7

    Outstanding

  • Sykes rating

Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights From £529

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

This spacious ground-floor apartment is nestled in the gorgeous seaside town of Weymouth in Dorset. Bike/kayak storage. En-suite. WiFi. Dorchester 6.3 miles; Isle of Portland 8.6 miles; West Lulworth 12.3 miles. (Ref. 1037083)

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


for 7 nights From £492

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

With off road parking for 2 cars and just a short 3-minute walk to the old harbour, town centre and beach beyond, this fully modernised 1900 cottage with 3 bedrooms, more importantly 3 bathrooms with 2 receptions and a sunny south facing garden is a steal (Ref. 1099795)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • £370 off - Sat 29th Aug to 5th Sep 2026


for 7 nights From £827

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    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)

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


for 7 nights From £552

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7

    Outstanding

  • Sykes rating

A stylish apartment resting on Weymouth's beautiful esplanade. Sleeps 4. Opposite beach. Off road parking. WiFi. Dorchester 7.3 miles; Bridport 20.3 miles. (Ref. 1067722)

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


for 7 nights From £631

Last booked yesterday
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