Chiswell On Portland Holiday Cottages

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Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 346 cottages

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Map View
A window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour
42
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1107011)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £476

Last booked yesterday
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A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Sykes Rating

The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. Designated parking. Close to a beach and amenities. Enclosed garden. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1133998)

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

7 nights from £653

Last booked 9 hours ago
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A row of multi-colored buildings along a waterfront with a boat named Top Cat III docked at Safe Harbour Brewers Quay harbour
33
Brewers Quay harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Sykes Rating

Cosy, comfortable and luxurious three storey house in Weymouth. Perfect for families. WiFi. Courtyard. One dog welcome. Pub and shop 5 min. Beach 10 min. Dorchester 8 miles. (Ref. 994606)

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

7 nights from £946

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A brick exterior of a cottage with white doors and windows at Rupert Cottage Brewers Quay harbour
27
Brewers Quay harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

Sleeping 4 cosy cottage in Weymouth. Close to harbour and all amenities. Gated development. (Ref. 994605)

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

7 nights from £595

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Three modern two story houses with green window frames and stone wall facades with a paved driveway and some plants at Pebbles Reach in Fortuneswell
42
Fortuneswell, Dorset, DT5
  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.6

    Sykes Rating

An attractive, terraced, three-storey house near Chesil Beach in Fortuneswell, Dorset. Off-road parking. Dog-friendly. Enclosed terrace. Smart TV. Bedroom with en-suite. Weymouth 4.6 miles. (Ref. 1091335)

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

7 nights from £737

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An outdoor patio area with a wooden table and six wooden chairs in front of a modern concrete structure with large sliding glass doors at Standby Generator Bunker Ringstead near Weymouth
67
Ringstead near Weymouth, Dorset, DT2
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0

    Sykes Rating

Standby Generator Bunker, an impressive abode, rests in rural Ringstead in Dorset, enjoying sea views, a pet-friendly policy, and a woodburning stove. Dorchester 8.3 miles; Bridport 23.1 miles. (Ref. 1137374)

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

7 nights from £1076

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A coastal view with boats on water and a hill in the background at Portland Pebble in Wyke Regis
43
Wyke Regis, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Sykes Rating

An enticing, semi-detached house sitting in Wyke Regis, Dorset. Sea views. Near the beach and coast. Balcony. Weymouth 3.3 miles; Isle of Portland 3.8 miles; Dorchester 10.3 miles. (Ref. 1097679)

  • Wi-fi
  • Off-road parking

7 nights from £740

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Two armchairs with striped cushions by bay windows overlooking a beach at Three @ No36 in Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Sykes Rating

Three @ No36, a delightful, second-floor apartment situated in the town of Weymouth in Dorset, enjoying sea views with the beach on your doorstep. Smart TV. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162204)

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

7 nights from £606

Last booked 5 hours ago
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A small blue house with patio furniture and potted plants on a tiled patio at Outlook Lodge in Bowleaze
28
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

A lodge sleeping four people, Bowleaze area of Weymouth. Dog friendly. Large garden. Parking for two cars. (Ref. 994500)

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

7 nights from £783

Last booked yesterday
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A street corner with rows of attached houses and a blue building in the background at Shrimp Cottage in Brewers Quay Harbour
Offer
49
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0

    Sykes Rating

Shrimp Cottage is a tasteful house in Brewers Quay Harbour, Dorset, this pet-friendly abode boasts Smart TVs and is near the beach and other amenities. Dorchester 9 miles; West Lulworth 15.9 miles (Ref. 1173548)

  • Wi-fi
  • Dishwasher
  • Washing machine

  • 15% off - Fri 25th Jul to 22nd Aug 2025

7 nights from £651

Last booked 2 days ago
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A balcony with two chairs a table with a bottle of champagne and glasses overlooking greenery and water at Waters Edge in Wyke Regis
35
Wyke Regis, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8

    Sykes Rating

Modern family house located on the edge of Weymouth, with sea views. Short drive to town centre. Welcomes two dogs. Garden. Pub and shop 10 min. Beach 2 min. Bridport 19 miles. (Ref. 994759)

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

7 nights from £631

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A brick house exterior with white framed windows a door a mailbox and a small outdoor table with a bench at Goliath in Brewers Quay Harbour
24
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

Beautiful 1 bedroom stable conversion in the heart of the harbour area in Weymouth. WIFI, Close to town centre and beach. Parking for one car. (Ref. 1096825)

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

7 nights from £494

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A corner seating area with two black armchairs near bay windows and a side table with a lamp at Two @ No36 in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Sykes Rating

Two @ No36, a wonderful, first-floor apartment situated in the heart of Weymouth in Dorset, with the beach on your doorstep. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162203)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £641

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A living room with two grey sofas and a wooden boat-shaped shelf with books at Chesil Retreat Weymouth
32
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Sykes Rating

A stylish property resting in the resort of Weymouth, Dorset. Enclosed garden. Pet free. Beach nearby. Dorchester 10.1 miles; Bridport 18.8 miles. (Ref. 1100742)

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

7 nights from £599

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A row of brick houses with white windows and a blue door at ODYSEA in Weymouth
49
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Sykes Rating

Just a 3-minute walk to the old harbour, town bridge and beach beyond this fully modernised mid terrace cottage includes three beds, three bathrooms and two off-road parking spaces.. Dorchester 8.4 miles; Bridport 18.9 miles. (Ref. 1099795)

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

7 nights from £768

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The front view of a two-story brick house with a green door and multiple windows and a paved driveway at Bridge Apartment in Weymouth
20
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

Ground Floor modern accommodation. Near to Weymouth Town centre and nature reserve. Perfect for families or couples. Allocated parking. Modern property. WIFI. (Ref. 994034)

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

7 nights from £446

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Stone buildings covered with greenery along a street with a white gate at Market House in Abbotsbury
43
Abbotsbury, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Sykes Rating

This wonderful renovated cottage is situated in the village of Abbotsbury, near the coastal town of Weymouth, Dorset. Rustic, cosy interior. stove, Weymouth 8.8 miles. (Ref. 992021)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £593

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A two-story house with a pitched roof on Hillcrest Road with a 20 mph zone sign and plants in Wyke Regis
46
Wyke Regis, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Sykes Rating

A fabulous three-bedroom holiday home in Wyke Regis, Dorset. Pet-friendly. Sea views. Close to beach and amenities. Open-plan. Contemporary. Weymouth 2.2 miles; Dorchester 9.6 miles. (Ref. 1103441)

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

7 nights from £763

Last booked yesterday
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A row of colorful terraced houses with blue cream pink and white facades on a cobblestone street at Harbour Tales in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Sykes Rating

A beautiful terraced fisherman’s cottage resting in the coastal town of Weymouth, Dorset. Close to a beach. Close to a pub. TV. Dorchester 8.4 miles; West Bay 18.1 miles, Lyme Regis 32.6 miles. (Ref. 1133009)

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

7 nights from £568

Last booked yesterday
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Front entrance of Bay View Hotel with brick buildings and ivy on walls in Weymouth
49
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    Sykes Rating

One @ No36 is a delightful duplex apartment with the beach on your doorstep, with the convenience of off-road parking, in Weymouth, Dorset. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162201)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £713

Last booked 2 days ago
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Map View

Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.