Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 341 cottages

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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

    4.7★

    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 £573

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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 £535

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A garden with a lawn and shrubs beside a white house with a glass porch at Skylark in Portesham
42
Portesham, Dorset, DT3
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

This fantastic detached bungalow is located in Portesham, Dorset. Sea views. Open fire. Off-road parking. Weymouth 7.7 miles; Dorchester 7.7 miles. (Ref. 1076553)

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


for 7 nights £978

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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

    4.3★

    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 £844

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A two story detached house with bay windows and a central front door with plants on each side at Family House in Weymouth
46
Weymouth, Dorset, DT3
  • Sleeps12
  • Bedrooms6
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

A spacious, detached, three-storey house nestled in Weymouth, Dorset. Close to amenities. Close to beach. Pet-free. Enclosed garden. Dorchester 6.5 miles; Bridport 18 miles. (Ref. 1080182)

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


for 7 nights £1273

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A bungalow with a front yard at 7 Cedar Drive Preston
36
Preston, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Cedar Drive is a charming house in Preston, Dorset, boasting ground-floor living, close proximity to local amenities and the coast for great days out. Weymouth 3.6 miles (Ref. 1173784)

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


for 7 nights £608

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A living room with a sofa, coffee table, and dining area at Beachcomb in Weymouth
29
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 £449

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An outdoor space with an inflatable hot tub surrounded by plants and decorative panels on the walls at North Harbour House in Weymouth
27
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

An end-of-terrace, three-storey property nestled just paces from the harbour in Weymouth, Dorset. Child-friendly. Hot tub. Close to amenities and beach. Dorchester 8.2 miles; Bridport 20.4 miles. (Ref. 1097631)

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


for 7 nights £804

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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 £1059

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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
  • Sleeps4
  • Bedrooms3
  • PetsYes

    3.3★

  • 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 £618

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Exterior view of connected residential buildings with bay windows and tiled roofs at Star Fish Apartment in Weymouth
17
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.1★

    Good

  • Sykes rating

Comfortable first floor apartment close to Weymouth town centre. Quiet location. WiFi. Parking for one car. Pub, shop, beach 10 min. Dorchester 7 miles. (Ref. 994671)

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


for 7 nights £421

Last booked yesterday
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A brick house with a red door and white framed windows behind a stone wall at Weybury Cottage in Brewers Quay Harbour
18
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.3★

    Good

  • Sykes rating

A period three-storey terraced property resting in Weymouth, Dorset. In walking distance of amenities and beach. Pet-friendly. Isle of Portland 6.1 miles; Dorchester 8.7 miles. (Ref. 1055214)

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


for 7 nights £629

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A coastal town with rooftops and flowers in the foreground at 33 High Street in Fortuneswell
39
Fortuneswell, Dorset, DT5
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

33 High Street is a well-positioned, three-bedroom home resting in Fortuneswell, Dorset. Near amenities and the beach. Contemporary. Pet-friendly. Enclosed garden. Near AONB. Weymouth 4.9 miles. (Ref. 1138399)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £578

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A harbor scene with boats under a bridge and buildings along the waterfront at Old Harbour View Brewers Quay Harbour
21
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    3.8★

    Good

  • Sykes rating

Harbourside first floor apartment with balcony. Centrally located for all bars and restaurants. WiFi. Sleeps 4. (Ref. 994482)

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


for 7 nights £645

Last booked 2 days ago
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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

    4.3★

    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 £465

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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 £532

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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 £670

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An outdoor view of a house with a table and chairs at Driftwood in Weymouth
27
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

Driftwood is a delightful, terraced holiday home situated in the popular coastal town of Weymouth in Dorset, set just a short walk from the beach. Dorchester 8.1 miles; Bridport 20.2 miles. (Ref. 1173824)

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


for 7 nights £487

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A row of terraced houses with different colored facades on a paved street 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 £631

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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

  • 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

  • 5% off - Fri 21st Feb to 31st Dec 2025


for 7 nights £533

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