Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 345 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

An immaculate second-floor apartment resting in the centre of Weymouth. Marina views. Open-plan living room. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059264)

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

7 nights from £649

  • Sleeps6
  • Bedrooms4
  • PetsNo

    4.7

    Sykes Rating

Spindrift is a characterful, home resting upon Brewers Quay Harbour in Dorset. Original features. Close to amenities, attractions and the harbour. Balcony. Dorchester 8.5 miles; West Lulworth 15.3 miles. (Ref. 1137640)

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

7 nights from £665

  • Sleeps4
  • Bedrooms2
  • PetsNo

    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

7 nights from £593

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5

    Sykes Rating

This fabulous three-bedroom abode resides in Weymouth, Dorset. Sea glimpses. Smart TV. Open-plan. Near an AONB. Dorchester 7 miles; Bridport 19.5 miles. (Ref. 1125198)

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

7 nights from £679

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8

    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
  • 10% off - Sat 28th Jun to 22nd Jul 2025

7 nights from £594

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    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. 994451)

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

7 nights from £768

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Sykes Rating

Located on the harbourside, is this two-bedroom contemporary apartment in Weymouth, Dorset. Off-road parking. WiFi. Fortuneswell 4.7 miles; Dorchester 9.3 miles. (Ref. 1017563)

  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • 10% off - Thu 29th May to 31st Aug 2025

7 nights from £809

7 nights from £486

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.4

    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 £628

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. Walking distance to town centre. Pub, shop 5 min. Beach 10 min. Dorchester 8.3 miles. (Ref. 994737)

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

7 nights from £717

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Sykes Rating

Victoria House is a pleasant holiday home resting in the coastal town of Weymouth in Dorset. Public car parking. Over three floors. Near amenities. Dorchester 8 miles; Bridport 20.2 miles. (Ref. 1148491)

  • Wi-fi

7 nights from £459

7 nights from £557

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    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

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.2

    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 12th Jul to 26th Jul 2025

7 nights from £842

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Sykes Rating

Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weymouth. Open plan living, en-suite facilities, private patio. Furnished and equipped to a very high standard. Weymouth 3.5 miles. (Ref. 932157)

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

7 nights from £616

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    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

7 nights from £526

7 nights from £625

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Sykes Rating

Tucked in a quiet location in Weymouth, The Pines is a modern holiday home for families or couples. Welcomes two dogs. Pub and shop 10 mins. Beach 1 mile. Dorchester 9 miles. (Ref. 994549)

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

7 nights from £637

Last booked yesterday
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.5

    Sykes Rating

Stylish fisherman’s cottage just a few minutes’ walk from Old Harbour in Weymouth. Beach 1 mile. Harbour, shop and pub 5 min. Welcomes one dog. Poole 33 miles. (Ref. 1058438)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £579

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    Sykes Rating

Large kitchen diner. Beautiful rural location. Short walk to the sea. Wi-Fi. In the heart of the Jurassic coastline. Picture postcard thatched cottage. (Ref. 994553)

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

7 nights from £946

Last booked 2 days ago
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