Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 351 cottages

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A sandy beach with tire tracks and footprints beside a paved promenade with pedestrians and buildings at Sunrise Apartment in Weymouth
Offer
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A contemporary first-floor apartment overlooking the coast in Weymouth, Dorset. Open-plan. Sea views. WiFi. Close to amenities. Dorchester 7.4 miles; Bridport 20.2 miles. (Ref. 1097676)

  • Wi-fi

  • 5% off - Sat 18th Apr to 22nd May 2026


for 7 nights $723

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A two-story brick house with a white enclosed porch shrubs in front and a driveway leading to a detached garage at Casa Carmen in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.2★

    Good

  • Sykes rating

Modern, detached cottage resting on the edges of Weymouth in Dorset. Off-road parking. Garden. WiFi. Close to harbour, shops, restaurants and pubs. (Ref. 1001584)

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


for 7 nights $872

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A stone cottage with a wooden door and white framed windows with a stone wall and gate in front at Blueberry Cottage in Sutton Poyntz
Offer
28
Sutton Poyntz, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

An enchanting refurbished cottage in the centre of the lovely village of Sutton Poyntz. Fully furnished and comfortable. Sunny patio garden. WiFi. Weymouth 4 miles. (Ref. 994009)

  • Wi-fi
  • Dishwasher
  • Washing machine

  • 15% off - Fri 1st May to 31st Jul 2026


for 7 nights $621

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A white cottage with a thatched roof and potted plants outside on a roadside at Amy Cottage in West Lulworth
43
West Lulworth, Dorset, BH20
  • Sleeps6
  • Bedrooms4
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Amy Cottage is a beautiful thatched cottage with a toasty gas fire and accepting pets, located in Dorset's West Lulworth on the Jurassic coastline. Wareham 8.7 miles; Weymouth 14.6 miles. (Ref. 1166887)

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


for 7 nights $1079

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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


for 7 nights $1349

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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


for 7 nights $786

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Exterior view of a stone and brick house with a thatched roof and gravel courtyard at Little Forge in West Lulworth
29
West Lulworth, Dorset, BH20
  • Sleeps5
  • Bedrooms2
  • PetsNo

    4.4★

    Good

  • Sykes rating

Modern, beautiful thatched cottage. Inglenook fireplace. Local activities only a short drive away. Nearby pubs and restaurants. Ensuite bedrooms. (Ref. 994342)

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


for 7 nights $871

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Weymouth Bay Apartment C - 994773 - photo 1
34
Greenhill, Dorset, DT4
  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Second floor comfy apartment sleeping 7 guests close to the sea in Weymouth. Welcomes two dogs. Garden. Beach 2 min. Shop 10 min. Pub 5 min. Dorchester 7.6 miles. (Ref. 994773)

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


for 7 nights $752

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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


for 7 nights $884

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A living room with a blue armchair a colorful armchair a television a small fireplace and blue curtains at The Skipper's House in Weymouth
36
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

A delightful, three bed property nestled in the heart of Weymouth, Dorset. Enclosed courtyard. Washing machine. Smart TV. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1132346)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $617

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A garden with grass and flowerbeds in front of a blue bungalow with a veranda and outdoor chairs at Harbour View Bungalow in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Overlooking the beautiful Nothe Gardens and, through the trees, the coastal views of Weymouth Bay and Portland Harbour is Harbour View Bungalow. (Ref. 994244)

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


for 7 nights $1608

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A brick exterior with white doors windows hanging plants and a sculpture at Barley Mews Brewers Quay Harbour
50
Brewers Quay Harbour, Dorset, DT4
  • Sleeps9
  • Bedrooms4
  • PetsNo

    4.3★

    Good

  • Sykes rating

A beautiful conversion of the Devenish Brewery malthouse, just moments from the harbourside. Sleeps 9, WIFI, stylish curved kitchen. Games Room (Ref. 993976)

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


for 7 nights $1612

Last booked 2 days ago
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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


for 7 nights $1108

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A living room with teal sofas a wooden coffee table a television on a corner stand and a dining area with wooden chairs at Louisa Cottage Brewers Quay Harbour
23
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.4★

    Good

  • Sykes rating

Beautiful and spacious cottage over three floors in Weymouth. Next to the Old Harbour and close to town centre. Beach 1 mile. Pub and shop 5 min. Beach 1 mile. Dorchester 8.5 miles. (Ref. 994354)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights $776

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A brick house facade with a black door and five windows at Pixie Cottage in Weymouth
26
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A delightful Weymouth terraced cottage, sleeps 4, close to the harbour and walking distance to the beach. Wifi. Close to shops and restaurants. (Ref. 1132245)

  • Wi-fi
  • Washing machine


for 7 nights $714

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A front view of a large brick and white house with bay windows and a small porch at Dream View in Greenhill
24
Greenhill, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Located on the Esplanade in Weymouth with far reaching beach and sea views and within walking distance of the Harbour and town amenities. (Ref. 994167)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights $811

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A brick terraced house with a black front door two windows with shutters and a street lamp in front at Harbour Catch Cottage in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Traditional cute cottage, in the town centre side of Weymouth harbour. WIFI, Close to Shops, restaurants and bars. Perfect for a couples retreat. (Ref. 994240)

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


for 7 nights $678

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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


for 7 nights $960

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A balcony with a round glass table and wicker chairs overlooking a marina and trees at Sunset View in Castletown Portland
50
Castletown, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.3★

    Good

  • Sykes rating

Sunset View is a perfectly-positioned, fifth-floor apartment residing in Castletown, Dorset. Sea views. Close to amenities and the beach. Private balcony. Portland 2.1 miles; Weymouth 5 miles; Dorchester 12.4 miles. (Ref. 1141111)

  • Wi-fi
  • Dishwasher
  • Baby-friendly


for 7 nights $678

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A brick residential building with white doors and windows next to a small lawn and paved driveway at Lodmoor House in Weymouth
25
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A lovely two-bedroom house resting in Weymouth, Dorset. Family-friendly. Enclosed garden. Near a beach. Pet-friendly. Dorchester 6.7 miles; Bridport 19.6 miles. (Ref. 1120462)

  • Wi-fi
  • Washing machine


for 7 nights $629

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