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Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 348 cottages

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  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.7

    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 £627

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.7

    Sykes Rating

Lyme View, delightful coastal property resting in Fortuneswell on the Isle of Portland, Dorset. Close to a beach. Garden. Pet friendly. Close to a shop and a pub. Weymouth 5.2 miles; Abbotsbury 11.9 miles; Dorchester 12.8 miles. (Ref. 1135049)

  • Wi-fi
  • Electric vehicle charging
  • Washing machine

7 nights from £476

7 nights from £567

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.6

    Sykes Rating

Lovely thatched Grade II listed cottage for a family or friends. Welcomes two dogs. Inglenook fireplace and original beams. Beach 1 mile. Pub 5 min. Seasonal shop 10 min. (Ref. 994302)

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

7 nights from £702

  • 7 Guests
  • 3 Bedrooms
  • Pets No

    4.5

    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 £562

Last booked yesterday
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  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.8

    Sykes Rating

A fabulous three-bedroom holiday home in Wyke Regis, Dorset. Pet-friendly. Sea views. Close to beach and amenities. Open-plan. Contemporary. Weymouth 2.2 miles; Dorchester 9.6 miles. (Ref. 1103441)

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

7 nights from £763

7 nights from £414

  • 8 Guests
  • 4 Bedrooms
  • Pets No

    4.9

    Sykes Rating

This charming, four-bedroom holiday home rests in Weymouth, Dorset. Over three floors. Open plan. Off-road parking. Dorchester 8.5 miles; Bridport 19.2 miles. (Ref. 1043677)

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

7 nights from £1167

7 nights from £466

  • 6 Guests
  • 3 Bedrooms
  • Pets No

    4.5

    Sykes Rating

A delightful cottage situated next to Weymouth harbour in Dorset. Harbour Views. Family-friendly. Dorchester 8.4 miles; West Lulworth 15.5 miles. (Ref. 1061726)

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

7 nights from £821

  • 6 Guests
  • 3 Bedrooms
  • Pets No

    4.5

    Sykes Rating

A beautifully presented property just moments from Weymouth harbour and Netwon's Cove in Dorset. Near amenities. WiFi. Off-road parking. En-suite. Isle of Portland 6.1 miles; Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1056258)

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

7 nights from £637

7 nights from £637

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.7

    Sykes Rating

Old Harbour Townhouse, a delightful, three-storey abode set in the seaside town of Weymouth in Dorset. Near coast. Woodburning stove. Open-plan. Near pub. Dorchester 8.7 miles; Bridport 19.4 miles. (Ref. 1159836)

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

7 nights from £719

Last booked 2 days ago
See more details
  • 8 Guests
  • 3 Bedrooms
  • Pets No

    4.9

    Sykes Rating

On Weymouth Harbourside this is an extraordinarily spacious apartment, sleeps 8, tastefully renovated, Large en-suite showers to all rooms, harbour views, WiFi. (Ref. 994463)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Sat 19th Apr to 23rd May 2025

7 nights from £1043

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.8

    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
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Wed 16th Apr to 31st May 2025

  • 5% off - Sun 1st Jun to 30th Jun 2025

7 nights from £612

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.9

    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 £749

7 nights from £582

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.7

    Sykes Rating

A well-positioned, fourth-floor apartment resting in Castletown, Dorset. Sea views. Close to amenities and the beach. Contemporary. Designated parking. Private balcony. Portland 1.9 miles; Weymouth 5.2 miles; Dorchester 12.6 miles. (Ref. 1119638)

  • Wi-fi
  • Swimming pool
  • Dishwasher
  • Washing machine

7 nights from £552

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    Sykes Rating

Splash, a lovely, terrace cottage lies in the heart of Weymouth, a seaside town in Dorset. Near beach and pub. Smart TV. Near harbour. Dishwasher. Dorchester 8.6 miles; Bridport 19.4 miles. (Ref. 1154894)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £655

  • 10 Guests
  • 5 Bedrooms
  • Pets Yes

    Sykes Rating

26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. Smart TV. Pet-friendly. Sea views. Close to amenities. Dorchester 7.9 miles; Bridport 20.6 miles. (Ref. 1118900)

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

7 nights from £1230