Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 351 cottages

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A house with a garden and bench at Chenies, Osmington Mills, near Preston
40
Osmington Mills, near Preston, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Chenies is a traditional cottage in the delightful hamlet of Osmington Mills near Preston, Dorset. Sea views. Near a pub. Characterful. Open fire. Preston 2.8 miles; Weymouth 5.9 miles. (Ref. 1149628)

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


for 7 nights £460

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A large apartment building with green-tinted glass balconies and cylindrical glass elevator shafts along a street at Manhattan Beach in Castletown Portland
27
Castletown, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Manhattan Beach is an apartment with a balcony with sunning sea and marina vistas, on the edge of the village of Castletown, Isle of Portland, in Dorset. Portland 2.2 miles; Weymouth 5.5 miles; Dorchester 12.5 miles. (Ref. 1161472)

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


for 7 nights £607

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A backyard with a hot tub, a table with chairs, an umbrella, grass, trees, and a wooden fence at Cliffwalk Cottage in Southwell
26
Southwell, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2★

    Good

  • Sykes rating

This contemporary holiday home rests in Portland, Dorset. Hot tub. Barbecue. Near amenities. Pet-friendly. Easton 1.5 miles; Chiswell 3 miles; Weymouth 7.5 miles. (Ref. 1122555)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine


for 7 nights £485

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An outdoor hot tub next to a blue house with glass doors and a garden with grass and bushes at Fisherman's Cottage in Southwell
25
Southwell, Dorset, DT5
  • Sleeps6
  • Bedrooms3
  • PetsNo

  • Sykes rating

A historic, 18th-century cottage resting in Portland, Dorset. Sea views. Character features. Hot tub. Near a pub. Easton 1.5 miles; Chiswell 3 miles; Weymouth 8 miles. (Ref. 1122551)

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


for 7 nights £786

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A street with parked cars stone wall and houses overlooking the sea at Bowleaze View in Weymouth
30
Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.2★

    Good

  • 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


for 7 nights £878

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A brick townhouse with two bay windows a gray door and a black door at 15 Hardwick Street Weymouth
27
Weymouth, Dorset, DT4
  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A end-terrace house resting in Weymouth, Dorset. Close to beach. Enclosed garden. TVs in all bedrooms. Dorchester 7.4 miles; Bridport 19 miles. (Ref. 1049744)

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


for 7 nights £979

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A window with binoculars on the sill looking out to buildings a clock tower and a marina at Anchorage View in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Anchorage View is a stunning, two-bedroom property resting in Weymouth, Dorset. Pretty views. Near the Dorset AONB. Close to amenities and a beach. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1145912)

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


for 7 nights £555

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Stone cottage house with white door and windows surrounded by bushes at The Old Reading Room in Langton Herring
40
Langton Herring, Dorset, DT3
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.2★

    Good

  • Sykes rating

A charming semi-detached cottage in Dorset Village of Langton Herring, close to the Jurassic coast Upside down living, WiFi. Welcomes 1 well behaved dog. (Ref. 994488)

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


for 7 nights £776

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A stone walkway with plants along the side of a stone house at The Apple Loft at Jordan House in Preston
21
Preston, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.2★

    Good

  • Sykes rating

The Apple Loft at Jordan House is a contemporary cottage resting in Bowleaze, on the outskirts of Weymouth, Dorset. Off-road parking. Open-plan. Garden. Dorchester 6.1 miles; Abbotsbury 9.8 miles; Bridport 19.3 miles. (Ref. 1149531)

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


for 7 nights £516

Last booked today
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The exterior of a two story house with a balcony and tiled roof at Bayview Overcombe near Preston
19
Overcombe near Preston, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Bayview is a lovely first-floor apartment in Overcombe, near Preston, in Dorset, welcoming a pet and boasting stunning beach views from a balcony. Weymouth 2.1 miles. (Ref. 1159732)

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


for 7 nights £633

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The exterior corner of a building with blue beams a glass door partially open and a sign that reads Groves House at Groves House Castletown near Fortuneswell
17
Castletown near Fortuneswell, Dorset, DT5
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.2★

    Good

  • Sykes rating

Groves House is a lavish, reverse-level abode located in Castletown near Fortuneswell in Dorset, with an open-plan layout and only a short walk from a pub. Weymouth 5.6 miles. (Ref. 1166808)

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


for 7 nights £577

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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


for 7 nights £1410

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Stone cottage with thatched roof behind a metal gate and garden at Lychgate Cottage Osmington
Offer
42
Osmington, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3★

    Good

  • Sykes rating

Two bedroomed coastal village location. Accepts two dogs. Lawned garden. Beamed ceilings. (Ref. 994364)

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

  • 10% off - Sat 11th Apr to 18th Apr 2026

  • 15% off - Sat 25th Apr to 2nd May 2026


for 7 nights £740

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A living room with two blue sofas and a wooden coffee table next to a fireplace and dining area in the background at Day Cottage in Weymouth
40
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3★

    Good

  • Sykes rating

A delightful, terraced cottage nestled into the coastal town of Weymouth, Dorset. Open-plan living. Near amenities and beach. Close to attractions. Pet-friendly. Dorchester 8.4 miles; West Bay 18 miles; Lyme Regis 32.6 miles. (Ref. 1124105)

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


for 7 nights £452

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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 £627

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A row of attached houses with different exterior finishes on a street at Home From Home in Fortuneswell
57
Fortuneswell, Dorset, DT5
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

Home From Home is a delightful cottage nestled in the village of Fortuneswell in Dorset, Isle of Portland and is pet-friendly and near the beach. Weymouth 5.5 miles (Ref. 1158103)

  • Wi-fi
  • Washing machine


for 7 nights £495

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A patio with wooden chairs and a table outside a brick building with open double doors at Hide-A-Way in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Hideaway is a fine, single-storey annex situated in Weymouth, Dorset, with open-plan living, Smart TV, and well-positioned to nearby beaches and amenities. Dorchester 8.8 miles; Bridport 19.5 miles; Bournemouth 38.4 miles. (Ref. 1169910)

  • Wi-fi
  • Ground floor bedroom
  • Baby-friendly


for 7 nights £422

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A brick terraced house with a green front door and front lawn at The Lookout -The House With A View in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4★

    Good

  • Sykes rating

A well-presented, mid-terrace property resting within the village of Wyke Regis. Sea views. Pet-friendly. WiFi. Weymouth 2 miles; Dorchester 9 miles. (Ref. 1006910)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £677

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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 £607

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A stone and wood house with a tiled roof and grass in front at The Courthouse in Sutton Poyntz
20
Sutton Poyntz, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4★

    Good

  • Sykes rating

Detached property in village of Sutton Poyntz. 3 bedrooms. 2 dogs. Off road parking for two cars. (Ref. 994127)

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


for 7 nights £823

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