Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 346 cottages

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A balcony with wicker chairs a table and glass panels overlooking a harbor at Bears Apartment in Castletown Portland
27
Castletown, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Sykes Rating

A well-positioned, fourth-floor apartment resting in Castletown, Dorset. Sea views. Close to amenities and the beach. Contemporary. Designated parking. Private balcony. Portland 1.9 miles; Weymouth 5.2 miles; Dorchester 12.6 miles. (Ref. 1119638)

  • Wi-fi
  • Swimming pool
  • Dishwasher
  • Washing machine

7 nights from £537

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An exterior view of a stone cottage with benches and a gate with a Follis Cottage sign in Nottington
13
Nottington, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Sykes Rating

Comfortable cottage for couples or small family in Nottington, Dorset. Beaches and historic harbour 3 miles. Wifi. Lawn garden. Wheelchair access. (Ref. 994199)

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

7 nights from £499

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A brick residential building with multiple windows a gated entrance and a small staircase at Ocean Watch 1 in Greenhill
20
Greenhill, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Sykes Rating

Modern one level apartment. Sitting room, with balcony and beautiful sea views. Short walk to the beach and a causal walk to the town centre. Wifi. (Ref. 994505)

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

7 nights from £595

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A living room with two gray sofas a colorful rug a wooden coffee table and a wall-mounted television at Anchor Cottage in Brewers Quay Harbour
30
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Sykes Rating

A delightful 3 storey fishermans cottage that has been beautifully restored in the harbour area of Weymouth. (Ref. 993928)

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

7 nights from £631

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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

    4.8

    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

7 nights from £714

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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
17
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    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

7 nights from £631

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A marina with boats docked and buildings in the background at Harbourside Haven Apartment 2 in Weymouth
17
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    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

7 nights from £649

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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

    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

7 nights from £698

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A patio with a table and chairs set outside a house with open glass doors and a large plant at Park Mews Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

A stunning holiday home in the bustling seaside town centre of Weymouth in Dorset. Enclosed patio. Near beach. Smart TV. Isle of Portland 6.7 miles; Dorchester 8 miles; Bridport 20.2 miles. (Ref. 1054948)

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

7 nights from £526

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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
  • PetsNo

    4.6

    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

7 nights from £637

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A row of modern brick and beige townhouses with balconies and large windows behind a green hedge at Kiama in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Sykes Rating

A well-positioned, three-storey property resting in Weymouth, Dorset. Sea views. Close to amenities and the beach. Enclosed garden. Elevated position. Dorchester 8.9 miles; Bridport 20.6 miles. (Ref. 1118939)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £602

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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
  • PetsNo

    4.8

    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
  • Baby-friendly

7 nights from £578

Last booked yesterday
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An outdoor garden area with a gravel path picnic table plastic chairs and trees at Riverhouse Lodge in Upwey
21
Upwey, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Sykes Rating

A pretty village lodge, close to the seaside town of Weymouth in Dorset. Traditional. Beautiful Mediterranean-style garden. WiFi. Dorset AONB. Dorchester 4.9 miles. (Ref. 1017591)

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

7 nights from £493

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Exterior of a row of white buildings with balconies and doors including a restaurant named ENZO at Bliss On The Bay Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

A stylish apartment resting on Weymouth's beautiful esplanade. Sleeps 4. Opposite beach. Off road parking. WiFi. Dorchester 7.3 miles; Bridport 20.3 miles. (Ref. 1067722)

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

7 nights from £614

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A stone house with a tiled roof and a garage next to a paved driveway at St Johns View in Portland
19
Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Sykes Rating

St. John’s View is a modern holiday home in the Isle of Portland with sea views. Over lower ground floor and ground floor. Shop, pub, beach 5 min. Weymouth 4.6 miles. (Ref. 994677)

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

7 nights from £629

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A living room with leather sofas glass coffee table and a television near large windows overlooking boats at Harbourside Haven Apartment 4 in Weymouth
Offer
20
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

A stylish and contemporary apartment overlooking Weymouth Harbour in Dorset. Balcony. Underfloor heating. Smart TV. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059265)

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

  • 10% off - Sat 7th Jun to 2nd Aug 2025

7 nights from £666

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A living room with blue sofas a wooden coffee table and red rug by large windows overlooking the sea at Weymouth Bay in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4

    Sykes Rating

A well-appointed apartment resting in Weymouth, Dorset. Stunning sea views. Open-plan living. Isle of Portland 7miles. Dorchester 7.8 miles. Bridport 21.5 miles. (Ref. 1003082)

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

7 nights from £657

Last booked 2 days ago
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A brick house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
24
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

Situated in a gated complex near Weymouth harbour. WiFi. Parking. Close to bars and restaurants. (Ref. 994560)

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

7 nights from £582

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A balcony with a table and two chairs overlooking a harbor with boats and buildings at Harbourside Penthouse in Brewers Quay Harbour
21
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Sykes Rating

A contemporary and spacious third floor apartment on the Old Harbourside in Weymouth. Secure Private parking. Balcony. WiFi. Dorchester 7 miles; Bridport 17 miles. (Ref. 999829)

  • Wi-fi
  • Off-road parking

7 nights from £654

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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

    4.9

    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

7 nights from £499

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