Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 340 cottages

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A stone cottage with a white door and windows a wooden gate and gravel driveway at Little Brook in Nottington near Weymouth
26
Nottington near Weymouth, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsYes

    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)

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

7 nights from $709

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A small outdoor seating area with chairs and a table surrounded by flowers in front of a brick house with blue shutters at Garibaldi Cottage in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Garibaldi Cottage is a lovely, coastal home resting in the town of Weymouth in Dorset, enjoying close proximity to a nearby shop, beach, and pub. Dorchester 8.2 miles; Bridport 20.1 miles. (Ref. 1156408)

  • Wi-fi
  • Washing machine
  • Baby-friendly

  • 15% off - Wed 1st Oct to 1st Nov 2025

7 nights from $634

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Exterior view of a stone house with white framed windows a white garage door and a small porch at Fisherbridge Cottage Weymouth
39
Weymouth, Dorset, DT3
  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

This pretty, detached cottage lies in Preston, Dorset. Smart TV. En-suite master bedroom. Close to amenities. Woodburning stove. Weymouth 3.6 mile. (Ref. 1119018)

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

7 nights from $853

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A white two-story house with bay windows and a dark front door at Bay Cottage in Weymouth
50
Weymouth, Dorset, DT4
  • Sleeps9
  • Bedrooms4
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Bay Cottage is a well-presented, three-storey detached house situated in the resort of Weymouth, Dorset. Smart TV. Decking with furniture. Near a beach. Dorchester 8.4 miles; Bridport 20.3 miles. (Ref. 1139723)

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

7 nights from $1367

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A detached house with a double garage and driveway at Connaught Gardens in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

Large, modern house nestled on the outskirts of Weymouth, 1 mile from the beach and restaurants. Off-road parking. WiFi. Enclosed garden. (Ref. 1001446)

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

7 nights from $1025

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An outdoor dining area with a table and six chairs set in front of a bunker entrance with grass on the roof at The Transmitter Bunker in Ringstead
33
Ringstead, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

This quirky, converted bunker rests in Ringstead near Preston, Dorset. Open fire. In an AONB. Smart TV. Off-road parking. Weymouth 7.6 mile. (Ref. 1131689)

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

7 nights from $1157

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An outdoor patio with a table and chairs overlooking a garden and sea at Blue Yonder in Weymouth
37
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

Blue Yonder is a cheerful, terrace holiday home resting by the sea in Weymouth, Dorset. Sea views. Ground-floor living. Near beach. Close to pub. Dorchester 7.5 miles; Bridport 20.9 miles. (Ref. 1144628)

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

7 nights from $814

Last booked yesterday
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A living room with two gray sofas a colorful rug a wooden coffee table and a wall-mounted television at Anchor Cottage in Brewers Quay Harbour
30
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A delightful 3 storey fishermans cottage that has been beautifully restored in the harbour area of Weymouth. (Ref. 993928)

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

7 nights from $840

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A brick front house with a white door black door windows a bench and a paved driveway at Jay Cottage in Weymouth
37
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A lovely terraced house resting in a quiet residential area of Weymouth, Dorset. Enclosed garden. Pet-friendly. Near to beach. Dorchester 10.1 miles; Bridport 18.8 miles. (Ref. 1053611)

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

7 nights from $495

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A harbor with boats docked next to a row of buildings by the water at Monarch in Brewers Quay Harbour
39
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A delightful, romantic bolthole in the third-floor in Weymouth, Dorset. Balconies. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1078324)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $684

Last booked 2 days ago
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A stone house with a light blue door and white framed windows by a small river with ducks and overhanging trees at Duck Cottage in Sutton Poyntz
44
Sutton Poyntz, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. Pet-friendly. WiFi. Enclosed garden. (Ref. 1008404)

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

7 nights from $705

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An outdoor balcony with a table set with plates cups a teapot and pastries with buildings in the background at Spindrift Brewers Quay Harbour
38
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms4
  • PetsNo

    4.8★

    Outstanding

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

  • $135 off - Sat 25th Oct to 31st Oct 2025

7 nights from $855

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The exterior entrance of a red brick building with blue door and blue trim around windows at Seasides in Weymouth
55
Weymouth, Dorset, DT4
  • Sleeps13
  • Bedrooms6
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Lovingly renovated Seasides offers, beach, sea and harbour views, suitable for large family gatherings close to shops and amenities. (Ref. 1056791)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room
  • Sky TV

  • 20% off - Sun 9th Nov to 1st Dec 2025

  • 20% off - Mon 1st Dec to 21st Dec 2025

7 nights from $2184

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Two adjacent houses with black front doors and small porches with awnings and shrubs outside at Anvil House in Brewers Quay Harbour
25
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A pretty little modern house just a few minutes walk from the harbourside and local amenities. Close to the South West Coast Path. (Ref. 993929)

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

7 nights from $752

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A balcony with a round glass table and wicker chairs overlooking a marina and trees at Sunset View in Castletown Portland
50
Castletown, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.3★

    Good

  • Sykes rating

Sunset View is a perfectly-positioned, fifth-floor apartment residing in Castletown, Dorset. Sea views. Close to amenities and the beach. Private balcony. Portland 2.1 miles; Weymouth 5 miles; Dorchester 12.4 miles. (Ref. 1141111)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from $659

Last booked yesterday
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A row of terraced houses with white and yellow facades and a sidewalk at Brewers Quay Harbour
29
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6★

    Outstanding

  • 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 $1136

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A three-story red brick residential building with multiple white-framed windows and black doors at Admiral's Quarter Apartment 5 in Weymouth
11
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    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

7 nights from $574

Last booked yesterday
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A brick terraced house with a white front door gravel front garden and small plants at Home Waters in Wyke Regis
23
Wyke Regis, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

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

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

7 nights from $752

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A stone cottage with two windows a door and potted plants on a gravel yard with stone steps and greenery at Mill Cottage in Upwey
30
Upwey, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A charming reverse-level cottage in the village of Upwey, Dorset. Close to amenities. Woodburning stove. In an Area of Outstanding Natural Beauty. Romantic. Walkers & Cyclists. Weymouth 4.5 miles; Dorchester 4.6 miles. (Ref. 1072756)

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

7 nights from $705

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A two-story brick house behind a stone and brick wall with a black gate and a tree nearby at The Nook in Weymouth
40
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4★

    Good

  • Sykes rating

The Nook is a charming, pet-friendly cottage resting near the beach in the town of Weymouth in Dorset, boasting a woodburning stove and enclosed garden. Dorchester 8.5 miles; Bridport 20.5 miles; Poole 32.2 miles. (Ref. 1107935)

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

7 nights from $796

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