Chiswell On Portland Holiday Cottages

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Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 363 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published
A living room with a sofa and dining table at Red Rose Apartment in Weymouth
1 of 22
5
Weymouth, Dorset, DT4
  • Sleeps3
  • Bedrooms1
  • Pet FriendlyNo

  • Sykes rating

Red Rose Apartment is a centrally located apartment resting in Weymouth, Dorset and boasts parking, sea views and is within walking distance of the beach. Dorchester 7.8 miles; Bridport 19 miles. (Ref. 1190887)

  • Wi-fi
  • Washing machine


for 7 nights From $821

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A living room with two grey sofas and a wooden boat-shaped shelf with books at Chesil Retreat Weymouth
1 of 32
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    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


for 7 nights From $685

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A brick house with white framed windows and door with two black chairs and a small table outside at Nuke in Weymouth
1 of 22
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

This cottage boast style, character, and a fabulously contemporary interior. Central location. Surrounded by history. WiFi. Rodwell 0.9 miles. (Ref. 1005313)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From $889

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A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
1 of 33
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From $795

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A house with a front door and windows at The Weymouth House in Weymouth
1 of 28
5
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

  • Sykes rating

The Weymouth House is a welcoming holiday home in Weymouth, Dorset, with a private courtyard and parking permit. Dorchester 7.5 miles; Bridport 18.9 miles. (Ref. 1193951)

  • Pets go free
  • Wi-fi
  • Washing machine


for 7 nights From $2680

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A small dining area with a round table set for four near a window with a view of the beach and ocean at 5 The Beaches Weymouth
1 of 18
5
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

Beautiful seafront apartment within the popular resort of Weymouth in Dorset. Incredible sea views. WiFi. Centre of Weymouth. (Ref. 1003083)

  • Wi-fi
  • Dishwasher


for 7 nights From $677

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Stone terraced houses with white framed windows and a red door on a street at Bowman's Cottage Wakeham Portland
1 of 32
5
Wakeham, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From $686

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A living room with two sofas a round rug a wooden door and a shelf with books and a lamp at Kimberlin in Chiswell On Portland
1 of 46
5
Chiswell On Portland, Dorset, DT5
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights From $835

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A marina with boats and yachts docked and buildings in the background at Harbourside Haven Apartment 1 in Weymouth
1 of 18
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

A superb first-floor apartment resting in Weymouth, Dorest. Stunning marina views. Allocated off-road parking. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059262)

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


for 7 nights From $819

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The exterior entrance of a red brick building with blue door and blue trim around windows at Seasides in Weymouth
1 of 57
5
Weymouth, Dorset, DT4
  • Sleeps13
  • Bedrooms6
  • Pet FriendlyNo

    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 From $2833

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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
1 of 46
5
Weymouth, Dorset, DT4
  • Sleeps12
  • Bedrooms6
  • Pet FriendlyNo

    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 From $1585

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A row of terraced houses with flowers and bushes in front and a view of the sea at Langham Cottage in Portland
1 of 35
5
Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. Accepts one dog. Pub and shop 5 min. Beach 5 min. Bridport 23 miles. (Ref. 994321)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From $536

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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
1 of 22
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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


for 7 nights From $905

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Front entrance of Bay View Hotel with brick buildings and ivy on walls in Weymouth
1 of 49
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9★

    Outstanding

  • 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
  • Washing machine


for 7 nights From $1025

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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
1 of 27
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From $851

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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
1 of 41
5
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    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 From $831

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A living room with black leather sofas a glass coffee table with flowers and a lamp by the window at Harbourside Haven Apartment 3 in Weymouth
1 of 17
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

An immaculate second-floor apartment resting in the centre of Weymouth. Marina views. Open-plan living room. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059264)

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


for 7 nights From $804

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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
1 of 31
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From $989

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A dining table with flowers butter croissants orange juice and jam by windows overlooking a beach at Grandview in Weymouth
1 of 47
5
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

Easter Weekend open to book! A characterful first-floor apartment set on the Dorset coast, within the town of Weymouth. Outstanding sea views. Central location. Family-friendly. Isle of Portland 7 miles; Dorchester 7.2 miles; West Bay 18.1 miles. (Ref. 1049890)

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


for 7 nights From $1164

Last booked 2 days ago
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A marina with boats docked and buildings in the background at Harbourside Haven Apartment 2 in Weymouth
1 of 17
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6★

    Outstanding

  • Sykes rating

A beautiful and contemporary first-floor apartment overlooking the harbour in Weymouth, Dorset. Balcony with harbour views. Master with en-suite. Allocated parking space. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059263)

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


for 7 nights From $819

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.