Chiswell On Portland Holiday Cottages

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British Travel Award Winners!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 340 cottages

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Map View
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★

    Outstanding

  • 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

  • £183 off - Fri 2nd Jan to 9th Jan 2026


for 7 nights £608

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A wooden front door next to a window with shutters and a gray mailbox numbered 20 at Smugglers Cottage in Weymouth
27
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A contemporary, three-storey property resting by the harbour in Weymouth, Dorset. Gas Fire in Lounge, WiFi. Close to beach and amenities. Weymouth 1 mile; Dorchester 8.6 miles. (Ref. 1058500)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £696

Last booked 2 days ago
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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

    4.9★

    Outstanding

  • 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


for 7 nights £532

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Front exterior of a house with a black door two potted plants and pink flowers in a garden at 6 The Terrace Brewers Quay Harbour
42
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. Quality finish. Sea and harbour views. Enclosed garden. Raised elevation. Dorchester 8.5 miles; West Lulworth 15.5 miles. (Ref. 1096352)

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


for 7 nights £903

Last booked yesterday
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A garden with grass a wooden deck with a swing and a patio with chairs and a table at Blue Waters in Weymouth
25
Weymouth, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A delightful, one-bedroom holiday home resting in Weymouth, Dorset. Contemporary. Private garden. Romantic. Close to amenities and beach. Near AONB. Open-plan. Dorchester 7 miles; Bridport 20.8 miles. (Ref. 1133982)

  • Wi-fi
  • Dishwasher


for 7 nights £500

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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★

    Outstanding

  • 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


for 7 nights £778

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Front exterior of a brick house with white-framed windows and door and garden shrubs with black chairs and table outside at Splash in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Splash, a lovely, terrace cottage lies in the heart of Weymouth, a seaside town in Dorset. Near beach and pub. Smart TV. Near harbour. Dishwasher. Dorchester 8.6 miles; Bridport 19.4 miles. (Ref. 1154894)

  • Wi-fi
  • Off-road parking
  • Dishwasher

  • £332 off - Mon 29th Dec 2025 to 5th Jan 2026


for 7 nights £664

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A two-story corner house with a pink brick exterior and a bay window at Mermaid House in Brewers Quay Harbour
41
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

This stylish and neat holiday home rests in Brewers Quay Harbour in Weymouth, Dorset. Close to amenities and harbour. Pet-free. Garden. Dorchester 8.7 miles; West Lulworth 15.8 miles. (Ref. 1093760)

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


for 7 nights £677

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A living room with a grey sofa with colorful cushions a glass coffee table and a fireplace at Ocean Retreat in Weymouth
14
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A stylish and contemporary apartment set in the town of Weymouth, Dorset. Seaside setting. Fantastic views. Off-road parking. Fortuneswell 5.8 miles; Dorchester 7.2 miles; Bridport 20.9 miles. (Ref. 1072234)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £747

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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

    4.8★

    Outstanding

  • 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
  • Washing machine


for 7 nights £721

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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★

    Outstanding

  • 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


for 7 nights £475

Last booked 2 days ago
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Boats docked in a harbor in front of buildings including Old Coastguard Apartment 2 in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps8
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

On Weymouth Harbourside this is an extraordinarily spacious apartment, sleeps 8, tastefully renovated, Large en-suite showers to all rooms, harbour views, WiFi. (Ref. 994463)

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


for 7 nights £1024

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Stone terraced houses with white framed windows and a red door on a street at Bowman's Cottage Wakeham Portland
32
Wakeham, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A beautiful stone cottage, complete with garden on the quieter end of Portland, however situated on the main bus route to Weymouth and beyond. (Ref. 994021)

  • Wi-fi
  • Washing machine


for 7 nights £511

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A row of beige townhouses with black doors and green framed windows at Kimberlin in Chiswell On Portland
52
Chiswell On Portland, Dorset, DT5
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A contemporary townhouse situated just a stone’s throw from Chesil Beach. Pet-friendly. Three floors. Beach views. Weymouth 4.5 miles. (Ref. 1084822)

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


for 7 nights £637

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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

    4.6★

    Outstanding

  • 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


for 7 nights £611

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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

    4.9★

    Outstanding

  • 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


for 7 nights £663

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A row of brick terraced houses with bay windows and plants in front on a street at Seaside House in Weymouth
46
Weymouth, Dorset, DT4
  • Sleeps12
  • Bedrooms6
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Elegant end of terrace Georgian Townhouse located in Weymouth. Close to amenities. Off-road parking. Pet-free. Courtyard with furniture. Dorchester 7.2 miles; Bridport 20.5 miles. (Ref. 1071940)

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


for 7 nights £1180

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Stone goose sculpture on grass with white buildings and a lighthouse tower in the background at Old Higher Lighthouse Stopes Cottage in Portland Bill
55
Portland Bill, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic Coast. Amazing views. Shared access to lighthouse observatory. Shared use of seasonal outdoor heated pool and Jacuzzi. (Ref. 12494)

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


for 7 nights £661

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The exterior entrance of a red brick building with blue door and blue trim around windows at Seasides in Weymouth
55
Weymouth, Dorset, DT4
  • Sleeps13
  • Bedrooms6
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Lovingly renovated Seasides offers, beach, sea and harbour views, suitable for large family gatherings close to shops and amenities. (Ref. 1056791)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room
  • Sky TV


for 7 nights £2017

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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★

    Outstanding

  • 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


for 7 nights £767

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Map View

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