Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 347 cottages

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A row of brick houses with blue and turquoise front doors and white windows on a street at Chapelhay Cottage in Weymouth
40
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    3.8★

    Good

  • Sykes rating

Chapelhay Cottage is a lovely, terraced cottage nestled into the seaside town of Weymouth, Dorset. Close shop and a pub. Close to a beach. Jurassic Coast. Portland 5.9 miles; Dorchester 8.4 miles; Lyme Regis 28.3 miles. (Ref. 1131030)

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


for 7 nights $834

Last booked 2 days ago
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A front view of a brick house with a white door and blue garage door and a palm tree in the garden at Milton House in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.3★

    Good

  • Sykes rating

A homely, mid-terraced holiday property resting in Weymouth, Dorset. Off-road parking. Pet-free. Close to a beach and amenities. Dorchester 6.6 miles; Bridport 18.2 miles. (Ref. 1116564)

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


for 7 nights $811

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A garden area with a wooden picnic table and benches a stone patio with two black chairs and a small table outside a stone cottage with a tiled roof at Apple Tree Cottage in Upton near Ringstead Bay
21
Upton near Ringstead Bay, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.2★

    Good

  • Sykes rating

A charming single-storey cottage resting in Upton near Preston, Dorset. Dog-friendly. Off-road parking. Close to amenities. In an AONB. Weymouth 7 miles. (Ref. 1129333)

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


for 7 nights $621

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An aerial view of a building with a gravel driveway a parked car a fenced garden area and pathways surrounded by trees at Casterbridge Upwey near Weymouth
33
Upwey near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

Superb, modern semi-detached holiday cottage, one of five on-site, on the edge of the Dorset village of Upwey, near Weymouth. Tastefully furnished. En-suite, Smart TVs. Dog-friendly. Short drive to Weymouth beach. Weymouth 3.5 miles. (Ref. 932161)

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


for 7 nights $869

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A dining area with a long table set with plates glasses and bread surrounded by blue chairs and a kitchen with appliances and plants at Beachaven in Weymouth
48
Weymouth, Dorset, DT4
  • Sleeps15
  • Bedrooms7
  • PetsNo

  • Sykes rating

Beachaven is a charming holiday home, set over three floors, located in the popular resort of Weymouth in Dorset resting near the beach and amenities. Dorchester 7.6 miles; Bridport 19.2 miles. (Ref. 1151664)

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

  • 5% off - Fri 27th Mar to 3rd Apr 2026

  • 5% off - Fri 10th Apr to 17th Apr 2026


for 7 nights $1907

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A red brick residential building with multiple windows and a paved driveway near a tree at Flat 6 Thornlow Heights in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4★

    Good

  • Sykes rating

A well-appointed, first-floor apartment resting in Weymouth, Dorset. Sea glimpses. Close to amenities, attractions and beach. Stylish. Off-road parking. Open-plan living. Near AONB. Dorchester 8.6 miles; Bridport 18.6 miles. (Ref. 1123245)

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


for 7 nights $721

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A sitting room with sofas chairs and a round coffee table at Marina Vista in Weymouth
21
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    3.7★

    Good

  • Sykes rating

Centrally located first floor apartment with views over the marina in Weymouth, close to shops and beach. Wifi, Off road private parking. (Ref. 994383)

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


for 7 nights $877

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A red brick building with blue doors and white framed windows at Old Malthouse Apartment in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3★

    Good

  • Sykes rating

Old Malthouse Apartment, a practical apartment in the town of Weymouth, Dorset, with a Smart TV and is a short stroll to the beach, harbour, pub and shop. Dorchester 8.1 miles; Bridport 19.3 miles. (Ref. 1175711)

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


for 7 nights $860

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An outdoor hot tub with water and jets next to a wall with ivy and a door at Pebble Reef in Easton Portland
36
Easton, Portland, Dorset, DT5
  • Sleeps6
  • Bedrooms3
  • PetsNo

    3.8★

    Good

  • Sykes rating

A lovely three-bedroom cottage perched in Easton, Dorset. Smart TV. Near a beach. Electric fire. Close to amenities. Enclosed garden. Weymouth 7 miles. (Ref. 1122341)

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


for 7 nights $902

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A living room with a sofa, coffee table, and dining area at Beachcomb in Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Beachcomb is a fine third-floor apartment located close to a beach in the town of Weymouth in Dorset, well-positioned to nearby attractions and amenities. Dorchester 7.7 miles; Bridport 21.2 miles; Poole 31.2 miles. (Ref. 1083686)

  • Wi-fi
  • Washing machine


for 7 nights $734

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A building exterior with benches and gardens at Corvesgate Nottington near Weymouth
52
Nottington near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.3★

    Good

  • Sykes rating

Corvesgate is a tasteful property resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Shared garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105456)

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


for 7 nights $842

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Stone cottage with thatched roof and white door with windows at Laurel Cottage in Osmington
21
Osmington, Dorset, DT3
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.1★

    Good

  • Sykes rating

A charming thatched roof character cottage resting in the village of Osmington, Dorset. Off-road parking. Open-plan living. WiFi. Close to pub. Weymouth 4.4 miles; Dorchester 5.4 miles. (Ref. 1064960)

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


for 7 nights $668

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A dining area with a wooden table, chairs, a bench, and table settings next to a living room with a sofa and a wall-mounted TV at Cove Street Cottage in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A well-positioned, three-storey home resting in Weymouth, Dorset. Close to amenities, harbour, and the beach. Family-friendly. Stylish. Elevated terrace. Central. Dorchester 8.4 miles; Bridport 18.5 miles. (Ref. 1122030)

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


for 7 nights $857

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Sunny Croft - 977681 - photo 1
28
Broadmayne near Dorchester, Dorset, DT2
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Sunny Croft is a delightful 1930s bungalow in Broadmayne, near Dorchester, Dorset. Stunning countryside views. Hot tub. Large garden. Private parking. Dorchester 4 miles; Weymouth 7.5 miles. (Ref. 977681)

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


for 7 nights $1020

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A building with an outdoor seating area and garden at Overcombe Mill Nottington near Weymouth
47
Nottington near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Overcombe Mill is a wonderful lodge nestled into the countryside of Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105455)

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


for 7 nights $871

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A brick residential building with white front doors and windows surrounded by shrubs at 2 Bathsheba Terrace in Dorchester
28
Dorchester, Dorset, DT1
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

A charming two-bedroom holiday home settled in Dorchester, Dorset. Washing machine. Enclosed garden. Gas fire. Close to amenities. Weymouth 8.9 miles; West Bay 17.3 miles. (Ref. 1096658)

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


for 7 nights $606

Last booked 6 hours ago
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A living room with a blue sofa orange cushions a floral armchair green curtains a black fireplace and a wooden TV cabinet at Georgian Hideaway in Weymouth
32
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.3★

    Good

  • Sykes rating

Georgian Hideaway, a quirky abode situated in the seaside town of Weymouth in Dorset. Near beach. Near shop. Near pub. Enclosed garden. Pet-friendly. Dorchester 7 miles; Bridport 17 miles. (Ref. 1154207)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $807

Last booked yesterday
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A living room with a sofa, green armchair, round mirrors, dining table with dishes and wine bottle at The Cottage in Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.1★

    Good

  • Sykes rating

The Cottage is a charming, two-bedroom townhouse resting in Weymouth, Dorset. Close to amenities. Smart TV. Enclosed balcony. Dorchester 8.5 miles; Bridport 20.6 miles. (Ref. 1137088)

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


for 7 nights $844

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Stone row houses with front doors, windows, grass lawn, and a stone sign reading Chestnut Court in West Lulworth
21
West Lulworth, Dorset, BH20
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

A pleasant, first-floor apartment located in West Lulworth, Dorset. Close to beach. Dog-friendly. Washing machine. Wareham 8.8 miles; Weymouth 15.4 miles. (Ref. 1102852)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $776

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The entrance to a brick house with a black door a welcome mat a potted plant and a white bay window
42
Weymouth, Dorset, DT4
  • Sleeps9
  • Bedrooms5
  • PetsYes

  • Sykes rating

Weymouth Seaside House is a wonderful property in the town of Weymouth, Dorset, that welcomes pets and is close to the beach as well as several amenities. Dorchester 7.6 miles; Bridport 20.4 miles. (Ref. 1172322)

  • Wi-fi


for 7 nights $1414

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