Chiswell On Portland Holiday Cottages

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Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 361 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 two sofas a coffee table a TV and paintings on the wall at Harbour Watch 2 in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.3★

    Good

  • Sykes rating

Located on the harbourside, is this two-bedroom contemporary apartment in Weymouth, Dorset. WiFi. Fortuneswell 4.7 miles; Dorchester 9.3 miles. (Ref. 1017563)

  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights From $1099

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The exterior entrance of a red brick building with blue door and blue trim around windows at Seasides in Weymouth
57
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 $2813

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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
  • 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 $680

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A garden with tables and chairs at Beck House in Weymouth
New property
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

Beck House, a welcoming mews house within a secure gated development in the heart of Weymouth, just a short walk from the harbour, beach and amenities. Dorchester 1.3 miles; Bridport 20.3 miles. (Ref. 1201741)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From $687

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A window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour
45
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    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 From $647

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
31
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 $790

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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
  • 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 $899

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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
  • Pet FriendlyNo

  • 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 From $1004

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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
46
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
  • Baby-friendly


for 7 nights From $829

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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
  • 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 $660

Last booked 3 hours ago
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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
22
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 $891

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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
  • 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 $982

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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
  • Pet FriendlyNo

    4.9★

    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 $857

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A view of buildings and beach at 32 Bowleaze Coveway in Preston
Offer New property
33
Preston, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

Bella Rosa a house in Preston, Dorset, boasts an en-suite bedroom, parking, beach views and proximity to Dorset's beaches and amenities. Weymouth 1 mile. (Ref. 1199281)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine

  • 10% off - Mon 13th Jul to 31st Dec 2026


for 7 nights From $690

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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
  • 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 $812

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A beach with houses alongside at Cove Cottage in Weymouth
New property
35
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

  • Sykes rating

Cove Cottage is a well-located cottage in Weymouth, Dorset, boasting close proximity to the beach and easy access to local shops and nearby amenities. Dorchester 9.7 miles; Bridport 18.9 miles. (Ref. 1094256)

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


for 7 nights From $885

Last booked yesterday
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A marina with boats and yachts docked and buildings in the background at Harbourside Haven Apartment 1 in Weymouth
18
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 $813

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A living room with a sea view at Portland View in Portland Bill
21
Portland Bill, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

A beautifully presented apartment with stunning views across the bay and Portland Bill. Open-plan living. WiFi. Scenic views. Weymouth 7.8 miles. (Ref. 1201975)

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


for 7 nights From $695

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A brick apartment building with balconies and parking at Brewery View in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.5★

    Outstanding

  • Sykes rating

Brewery View is a stylish, first-floor apartment near the beach in Weymouth, Dorset, with an open-plan living space, balcony, and designated parking. Dorchester 8.8 miles; Bridport 19.4 miles. (Ref. 1189426)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From $696

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Front view of three terraced houses with plants and bushes in front at Kingfisher Cottage in Weymouth
19
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

A terrace property resting close to the beach and harbour in Weymouth. Allocated parking for two cars. WiFi. Fortuneswell 4.7 miles; Dorchester 8.9 miles. (Ref. 1038344)

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


for 7 nights From $649

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Map View

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