Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 341 cottages

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A row of terraced houses on a street with paved sidewalk and cobblestone road at Lobster Cottage Brewers Quay Harbour
30
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.4★

    Good

  • Sykes rating

Lovely and comfortable cottage next to the harbour in Weymouth. Wifi. Shop and pub 5 min. Beach 1 mile. Dorchester 8 miles. (Ref. 994351)

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

7 nights from €562

Last booked 2 days ago
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A stone cottage with a thatched roof near the coast with grass and gravel paths at Pitt Cottage Ringstead
30
Ringstead, Dorset, DT2
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Large kitchen diner. Beautiful rural location. Short walk to the sea. Wi-Fi. In the heart of the Jurassic coastline. Picture postcard thatched cottage. (Ref. 994553)

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

7 nights from €1091

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A stone cottage with a white front door and a paved pathway bordered by trimmed hedges at Knapp Cottage in Chickerell
39
Chickerell, Dorset, DT3
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A charming, three-bedroom cottage sitting in Chickerell, Dorset. Close to amenities. Enclosed garden. Off-road parking. Weymouth 3.3 miles; Abbotsbury 5.9 miles; Portland 7.2 miles. (Ref. 1086432)

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

7 nights from €749

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A wooden house with skylights and a small garden area surrounded by trees at Roman Lodge in Osmington
31
Osmington, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A bright and airy lodge resting in Osmington near Preston, Dorset. Open-plan. Close to beach. Pet-friendly. Weymouth 5.4 miles; Poole 23.4 miles; Bournemouth 29.1 miles. (Ref. 1093891)

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

7 nights from €776

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An outdoor area with a building featuring windows and doors at Lulstead Nottington near Weymouth
39
Nottington near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Lulstead is a lovely cottage resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105451)

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

7 nights from €797

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A driveway leading to a single-story brick house with a red door and a small front lawn at Sunny Haven in Preston
26
Preston, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A lovely two-bedroom bungalow resting in Preston, Dorset. Dog-friendly. Off-road parking. Private garden. Close to amenities. Weymouth 3.4 mile. (Ref. 1106680)

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

7 nights from €643

Last booked yesterday
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A brick and white semi detached house with bay windows and potted plants outside at Anchor House Weymouth
68
Weymouth, Dorset, DT4
  • Sleeps15
  • Bedrooms6
  • PetsYes

    4.3★

    Good

  • Sykes rating

Anchor House is a stunning, pet-friendly townhouse with a private hot tub in the heart of Weymouth, Dorset, close to local amenities and the beach. Dorchester 7.8 miles; Bridport 19.9 miles. (Ref. 1105510)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from €1788

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A living room with leather sofas glass coffee table and large windows overlooking a marina at Harbourside Haven Penthouse 1 in Weymouth
16
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4★

    Good

  • Sykes rating

An immaculate penthouse apartment resting in the centre of Weymouth, Dorset. WiFi. Views over the marina. Off-road parking. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059266)

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

7 nights from €687

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The front exterior of a brick house with several windows a wooden door and a white garage door at Mariners Rest in Weymouth
15
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Set in a lovely and quiet residential area of Weymouth, the house is a comfortable getaway for a family. One dog welcome. Wifi. Shop and pub 5 min. Beach 10 min. Dorchester 7 miles. (Ref. 994377)

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

7 nights from €664

Last booked yesterday
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A waterfront with boats and buildings including Buccaneer Cottage at Brewers Quay Harbour
23
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4★

    Good

  • Sykes rating

Pretty cottage in the heart of Weymouth. Harbour views. Near to local amenities and town centre. Close to Weymouth Beach. WiFi. Pets welcome. Dorchester 8.5 miles. (Ref. 994047)

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

7 nights from €828

Last booked 2 days ago
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A terrace with table and chair overlooking a street at Harbour Retreat in Weymouth
36
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Harbour Retreat is an eclectic first-floor apartment close to the harbour and beach, with roadside parking, in the heart of Weymouth in Dorset. Dorchester 8.3 miles; Bridport 20.5 miles. (Ref. 1164179)

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

7 nights from €660

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Exterior view of a stone and brick house with multiple windows and blue doors a patio with chairs a table and an umbrella and plants at The Gables in Brewers Quay Harbour
18
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms4
  • PetsYes

    4.3★

    Good

  • Sykes rating

Lovely 4 bedroom house in gated area. Close to Weymouth harbour. Secure gated parking for one car. Welcomes two dogs. WiFi. (Ref. 994213)

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

7 nights from €907

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A dining and living area with a round table set for four near large windows and a glass door overlooking an outdoor area with a lighthouse visible beyond at Coastguard View in Portland Bill
27
Portland Bill, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Coastguard View is a lovely holiday cottage resting near the coast in Portland Bill on the Isle of Portland, Dorset with a Smart TV and open-plan space. Easton 2.6 miles; Fortuneswell 3.6 miles; Weymouth 9.1 miles. (Ref. 1169819)

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

7 nights from €677

Last booked yesterday
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A house with stone and wooden exterior at Everdene Upwey near Weymouth
46
Upwey near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. En-suite, modern features. Shop and pub within walking distance. Weymouth 3.5 miles. (Ref. 932160)

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

7 nights from €799

Last booked yesterday
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A brick two-story house with balconies and a hedge in front at Harbour Reach 6 in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A wonderful apartment that sleeps up to three people resting in Weymouth, Dorset. Open-plan. Near a beach. Close to amenities. Dorchester 7.8 miles; Bridport 18.5 miles. (Ref. 1057385)

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

7 nights from €447

Last booked yesterday
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A living room with an orange armchair green sofa and ottoman wooden bookcase and hanging plants at Harbour Retreat in Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Harbour Retreat is a delightful three-storey cottage by the harbourside in Brewers Quay Weymouth, Dorset. Close to beach, shops and amenities. Dishwasher. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1139963)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €748

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A narrow street with houses on the right and a brick wall with plants on the left at Firkin Cottage Brewers Quay Harbour
22
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms4
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Comfortable renovated cottage with rear garden and close to the town centre. Garden with furniture. Pub 5 mins. Beach 1 mile. Dorchester 9 miles. (Ref. 994191)

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

7 nights from €592

Last booked 2 days ago
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A dining area with round wooden table and chairs next to sliding glass doors leading outside with sofas and kitchen stools in Mermaid Cottage in Wakeham Portland
29
Wakeham, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.0★

    Good

  • Sykes rating

Mermaid Cottage is a delightful, contemporary cottage close to a beach and amenities, in the village of Wakeham, on the Isle of Portland, in Dorset. Weymouth 7.2 miles; Dorchester 14.2 miles. (Ref. 1143548)

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

  • 10% off - Sat 30th Aug to 3rd Oct 2025

7 nights from €686

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A stone house with windows and a garden with bushes in front at Anchor Cottage in Weston Portland
35
Weston, Portland, Dorset, DT5
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Anchor Cottage is a traditional 19th-century Portland Stone cottage resting in the charming village of Weston, Portland, Dorset, with off-road parking. Fortuneswell 1.6 miles; Weymouth 7 miles; Dorchester 14.1 miles; West Bay 21.8 miles. (Ref. 1160217)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from €591

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An outdoor area with a wooden building and gravel pathway at Dirdale in Weymouth
45
Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Dirdale is a tasteful lodge resting in rural Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Shared garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105458)

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

7 nights from €785

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