Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 341 cottages

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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 £835

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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 £654

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A balcony dining setup with plates glassware fruit bowl and bread overlooking a harbor at 65 Ocean View in Castletown Portland
31
Castletown, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    3.7★

    Good

  • Sykes rating

A well-presented apartment with views over Portland Marina in Castletown, Dorset. Balcony. En-suite. Beach nearby. Portland 2.1 miles; Weymouth 5 miles. (Ref. 1136982)

  • Wi-fi
  • Washing machine


for 7 nights £482

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A brick house exterior with two white garage doors two upper windows and two front doors with canopies at Sea Pebbles in Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    3.6★

    Good

  • Sykes rating

Close to the harbour in Weymouth, Semi detached house, access to South West Coast path, WIFI, Close to shops, restaurants and café’s, suitable for families. (Ref. 994639)

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


for 7 nights £714

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A view of fields houses cars and the sea through a large window at Lighthouse View in Portland
26
Portland, Dorset, DT5
  • Sleeps2
  • Bedrooms1
  • PetsNo

    3.9★

    Good

  • Sykes rating

A lovely, second-floor apartment resting in Portland. Sea views. Pet free. Studio-style. Fortuneswell 2.7 miles; Weymouth 7.7 miles; Dorchester 15.3 miles; West Bay 22.9 miles. (Ref. 1099649)

  • Wi-fi
  • Off-road parking


for 7 nights £352

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A row of colorful waterfront houses with docks in front at The Boat House in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.0★

    Good

  • Sykes rating

A superb, Grade II listed house set on the harbour side in Weymouth. Sleeps 10. WiFi. Close to shop, café and pub. Dorchester 8.5 miles. (Ref. 1005020)

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


for 7 nights £1420

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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 £562

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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 £765

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A building with multiple doors and windows at Egdon Heath, Nottington near Weymouth
44
Nottington near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

  • Sykes rating

Egdon Heath is a wonderful property resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105450)

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


for 7 nights £631

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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 £641

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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 £449

Last booked yesterday
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A living room with blue chairs a wooden table dining set a large window with blinds and a view of the sea at The Kings Vista in Weymouth
21
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A contemporary first-floor apartment overlooking the scenic coast of Weymouth, Dorset. Open-plan. Views. Parking. Fortuneswell 5.6 miles; Dorchester 7.6 miles; Bridport 19 miles. (Ref. 1060926)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £724

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A black door with a heart-shaped wreath and rubber boots near the entrance at The Kiln House in Weymouth
27
Weymouth, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.3★

    Good

  • Sykes rating

A self-contained annexe resting in the popular resort of Weymouth, Dorset. Romantic. Quiet location. Wi-Fi. Washing machine. Dorchester 4.5 miles; Bridport 18.2 miles. (Ref. 1124162)

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


for 7 nights £412

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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 £573

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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

    4.2★

    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 £633

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A white two-story building with a blue door and black framed windows labeled Neptune Cottage in Fortuneswell
20
Fortuneswell, Dorset, DT5
  • Sleeps5
  • Bedrooms3
  • PetsYes

    3.8★

    Good

  • Sykes rating

Neptune cottage situated in the Isle of Portland is very cosy and comfortable. Perfect for dog walks. Beach 2 min. Welcomes two dogs. Pub 5 min, shop 10 min. Weymouth 5 miles. (Ref. 994425)

  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights £566

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A wooden house with a gray slate roof and patio furniture in a garden at Bramshurst in Upwey near Weymouth
32
Upwey near Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A beautiful terraced holiday home, one of five set around a courtyard, on the edge of Upwey, near Weymouth. Attractive, well-appointed and modern holiday cottage. Many attractions and activities within reach. Weymouth 3.5 miles. (Ref. 932159)

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


for 7 nights £622

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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 £714

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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

  • 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

  • 5% off - Fri 1st Aug to 30th Sep 2025


for 7 nights £572

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A corner with two purple chairs and a round glass table by windows with shutters overlooking the beach at High Tide in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps10
  • Bedrooms5
  • PetsNo

    3.6★

    Good

  • Sykes rating

Beautiful, Georgian seafront house, nestled in the lively town of Weymouth. Sea views. En-suite bedrooms. WiFi. Beach less than 50 metres away. (Ref. 1006583)

  • Wi-fi
  • Dishwasher
  • Baby-friendly


for 7 nights £1478

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