Chiswell On Portland Holiday Cottages

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 kitchen with a view of a street and houses at Flat 3
New property
27
Fortuneswell, Dorset, DT5
  • Sleeps2
  • Bedrooms1
  • PetsYes

  • Sykes rating

Seaview Sanctuary is a stylish ground-floor apartment in Fortuneswell, Dorset, boasting glorious sea views, an open-plan living space and a well-equipped kitchen. Weymouth 4.3 miles, Lyme Regis 30.3 miles, Swanage 31.4 miles. (Ref. 1197543)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher


for 7 nights $746

Last booked 2 days ago
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A large apartment building with green-tinted glass balconies and cylindrical glass elevator shafts along a street at Manhattan Beach in Castletown Portland
27
Castletown, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Manhattan Beach is an apartment with a balcony with sunning sea and marina vistas, on the edge of the village of Castletown, Isle of Portland, in Dorset. Portland 2.2 miles; Weymouth 5.5 miles; Dorchester 12.5 miles. (Ref. 1161472)

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


for 7 nights $813

Last booked yesterday
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Exterior view of a brick terraced house with blue door white window and small hedge at Leo's Place in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A well-presented property nestled in the heart of Weymouth, Dorset. Roadside parking. Enclosed patio. Dorchester 8.5 miles; Bridport 19.2 miles. (Ref. 1134491)

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


for 7 nights $799

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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 $1159

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A living room with a dining area and furniture at Home from Home near the Sea Weymouth
New property
40
Wyke Regis, Dorset, DT4
  • Sleeps8
  • Bedrooms4
  • PetsNo

  • Sykes rating

Home from Home near the Sea is a neat three-storey house resting in Wyke Regis, Dorset, featuring easy access to the beach and nearby local amenities. Weymouth 2.8 miles; Dorchester 10.2 miles. (Ref. 1200131)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights $1193

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A front entrance with a blue door and window at 23 The Maltings in Weymouth
New property
27
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Dolphin Cottage is a lovely cottage nestled into the bustling seaside town of Weymouth, Dorset, close to a shop, pub, local walks, and beaches. Fortuneswell 4.8 miles; Dorchester 8.9 miles; Bridport 19.5 miles. (Ref. 1179916)

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


for 7 nights $884

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A garden with a table and chairs on a deck at Little Gem in Weymouth
New property
39
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Little Gem, a romantic ground-floor apartment resting in Weymouth, Dorset, boasts stunning coastal views and proximity to the beach and local amenities. Dorchester 9.2 miles; Bridport 20.7 miles. (Ref. 1203646)

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


for 7 nights $858

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A red brick residential building with multiple windows and a paved driveway near a tree at Flat 6 Thornlow Heights in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4★

    Good

  • Sykes rating

A well-appointed, first-floor apartment resting in Weymouth, Dorset. Sea glimpses. Close to amenities, attractions and beach. Stylish. Off-road parking. Open-plan living. Near AONB. Dorchester 8.6 miles; Bridport 18.6 miles. (Ref. 1123245)

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


for 7 nights $681

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A living room with a staircase and a sofa at Harbourside in Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

Harbourside is a charming, dog-friendly, Grade II listed house in Weymouth, Dorset, set over three stories, with open-plan living and a private courtyard. Dorchester 8.8 miles; Bridport 18.9 miles. (Ref. 1172365)

  • Wi-fi
  • Washing machine


for 7 nights $597

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The exterior corner of a building with blue beams a glass door partially open and a sign that reads Groves House at Groves House Castletown near Fortuneswell
17
Castletown near Fortuneswell, Dorset, DT5
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.2★

    Good

  • Sykes rating

Groves House is a lavish, reverse-level abode located in Castletown near Fortuneswell in Dorset, with an open-plan layout and only a short walk from a pub. Weymouth 5.6 miles. (Ref. 1166808)

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


for 7 nights $658

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A dining area with a wooden table, chairs, a bench, and table settings next to a living room with a sofa and a wall-mounted TV at Cove Street Cottage in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A well-positioned, three-storey home resting in Weymouth, Dorset. Close to amenities, harbour, and the beach. Family-friendly. Stylish. Elevated terrace. Central. Dorchester 8.4 miles; Bridport 18.5 miles. (Ref. 1122030)

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


for 7 nights $863

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A stone cottage with a thatched roof and garden by the roadside at Badgers Cottage in Langton Herring near Chickerell
44
Langton Herring near Chickerell, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3★

    Good

  • Sykes rating

A characterful, thatched cottage resting in Langton Herring near Chickerell, Dorset. Original features. Close to amenities. Dorset AONB. Pet-friendly. Abbotsbury 4.5 miles; Weymouth 5.8 miles; Portland 9.3 miles; Dorchester 9.7 miles. (Ref. 1123272)

  • Wi-fi
  • Baby-friendly


for 7 nights $714

Last booked yesterday
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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 $1059

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A house with a front door and windows at The Weymouth House in Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

  • 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)

  • Wi-fi
  • Washing machine


for 7 nights $2797

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A street view showing the old boathouse and new boathouse buildings with the inner harbour and boats in the background at New Boathouse in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.3★

    Good

  • Sykes rating

Enjoyable holiday home close to the Old Harbour in Weymouth for large groups. Beach 10 min. WiFi. Roadside parking. Shop and pub 5 min. Poole 32.5 miles. (Ref. 994432)

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


for 7 nights $1168

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A living room with a dining table and kitchen appliances at Rodwell Holt in Weymouth
New property
29
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Rodwell Holt, a pleasing first-floor apartment in Weymouth, Dorset, features a balcony and offers easy access to the harbour, beach, and local amenities. Dorchester 8.1 miles; Bridport 21.5 miles. (Ref. 1191754)

  • Wi-fi
  • Dishwasher
  • Baby-friendly


for 7 nights $707

Last booked yesterday
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An outdoor hot tub with water and jets next to a wall with ivy and a door at Pebble Reef in Easton Portland
36
Easton, Portland, Dorset, DT5
  • Sleeps6
  • Bedrooms3
  • PetsNo

    3.8★

    Good

  • Sykes rating

A lovely three-bedroom cottage perched in Easton, Dorset. Smart TV. Near a beach. Electric fire. Close to amenities. Enclosed garden. Weymouth 7 miles. (Ref. 1122341)

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


for 7 nights $908

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A view of the beach and sea with boats anchored offshore and greenery in the foreground at Castle Cove Cottage in Weymouth
41
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    3.9★

    Good

  • Sykes rating

A coastal cottage resting in Weymouth, Dorset. Close to the beach. Sea views. Balcony. Isle of Portland 5.4 miles; Dorchester 8.7 miles; Bridport 19 miles. (Ref. 1092544)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights $1121

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A living room with a sofa and dining table at Red Rose Apartment in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps3
  • Bedrooms1
  • PetsNo

  • 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 $1205

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A building facade with windows and entrance at Number 3 by the Sea in Weymouth
New property
34
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Number 3 by the Sea is an inviting ground‑floor apartment located in Weymouth, Dorset, boasting sea views, a front patio and direct access to the beach. Dorchester 7.6 miles; Bridport 19 miles. (Ref. 1203393)

  • Wi-fi
  • Ground floor bedroom


for 7 nights $794

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