Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 341 cottages

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A beachfront with a stone barrier green garden and a small gate at Weymouth Bay Apartment C in Greenhill
19
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 £605

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A white three-story residential building with a black and white tiled walkway leading to a black door at 66 3 Compass Point in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

3 Compass Point is a stylish, ground-floor apartment resting in Weymouth, Dorset. Near beach and amenities. Contemporary. Open-plan. Private parking. Dorchester 6.7 miles; Bridport 20.5 miles. (Ref. 1129014)

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


for 7 nights £664

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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 £559

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A house with a front door and gravel driveway at Coastguard Lookout in Wyke Regis
43
Wyke Regis, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Coastguard Lookout is a modern, reverse-level house near a beach in Wyke Regis, Dorset, with off-road parking, Juliet balcony, and underfloor heating. Weymouth 2.5 miles; Dorchester 9.6 miles. (Ref. 1169223)

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


for 7 nights £507

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A stone cottage with a thatched roof and a wooden table and benches outside at Magnolia Cottage Osmington
41
Osmington, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.1★

    Good

  • Sykes rating

Magnolia cottage is situated in Osmington. Pretty, thatched and very well-equipped. High chair and cot. Wifi. Parking for two cars. Pub 5 min. Weymouth 4.5 miles. (Ref. 994367)

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


for 7 nights £566

Last booked yesterday
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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

    4.5★

    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 £792

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A living room with a brown sectional sofa and decorative pillows a wooden coffee table with cups and a teapot two large windows with white shutters and a blue bean bag at Sunrise Apartment in Weymouth
36
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    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


for 7 nights £523

Last booked yesterday
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A stone cottage with a thatched roof a black door and two windows surrounded by plants and a gravel driveway at Little Ivy in West Lulworth
18
West Lulworth, Dorset, BH20
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.4★

    Good

  • Sykes rating

Pretty thatched cottage sleeping three people in beautiful West Lulworth village. Garden. Welcomes two well-behaved dogs. Parking for one car. Pub 5 min. Wareham 9 miles. (Ref. 994330)

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


for 7 nights £485

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Stone cottage with thatched roof behind a metal gate and garden at Lychgate Cottage Osmington
42
Osmington, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2★

    Good

  • Sykes rating

Two bedroomed coastal village location. Accepts two dogs. Lawned garden. Beamed ceilings. (Ref. 994364)

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


for 7 nights £625

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A blue painted two storey building with bay windows and white doors with black railings in front at Harbour Watch Apartment 1 Brewers Quay Harbour
23
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.2★

    Good

  • Sykes rating

A lovely apartment perfect for couples in Weymouth. Close to the town centre. Off-road parking for one car. WiFi. Pub and shop 5 min. Beach 1 mile. Dorchester 8 miles. (Ref. 994289)

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


for 7 nights £594

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A single-story house with a garage and front garden under a sunny sky at Hill View in West Lulworth
39
West Lulworth, Dorset, BH20
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A pleasant two-bedroom property based in West Lulworth, Dorset. Enclosed garden. Close to amenities and beach. In an AONB. Wareham 8.5 miles; Weymouth 15.4 miles (Ref. 1117992)

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


for 7 nights £520

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A street view of row houses with brick walls and bay windows with plants in front at Sandsfoot Rest in Weymouth
26
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

An attractive, Edwardian terraced house situated in Weymouth, Dorset. Woodburner. WiFi. Pet-friendly. Dorchester 7 miles; Bridport 17 miles. (Ref. 1001484)

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


for 7 nights £585

Last booked yesterday
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A front view of a brick house with a white door and blue garage door and a palm tree in the garden at Milton House in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.3★

    Good

  • Sykes rating

A homely, mid-terraced holiday property resting in Weymouth, Dorset. Off-road parking. Pet-free. Close to a beach and amenities. Dorchester 6.6 miles; Bridport 18.2 miles. (Ref. 1116564)

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


for 7 nights £610

Last booked 2 days ago
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A stone and wood house with a tiled roof and grass in front at The Courthouse in Sutton Poyntz
20
Sutton Poyntz, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.3★

    Good

  • Sykes rating

Detached property in village of Sutton Poyntz. 3 bedrooms. 2 dogs. Off road parking for two cars. (Ref. 994127)

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


for 7 nights £765

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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

    4.4★

    Good

  • 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 £498

Last booked yesterday
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Stone cottage with thatched roof and white door with windows at Laurel Cottage in Osmington
21
Osmington, Dorset, DT3
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.1★

    Good

  • Sykes rating

A charming thatched roof character cottage resting in the village of Osmington, Dorset. Off-road parking. Open-plan living. WiFi. Close to pub. Weymouth 4.4 miles; Dorchester 5.4 miles. (Ref. 1064960)

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


for 7 nights £460

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A living room with a blue sofa and television at Saddlers Cottage in Weymouth
17
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

A well-positioned, two-bedroom home resting in Weymouth, Dorset. Close to amenities, attractions and beach. Pet-friendly. Near AONB. Enclosed small courtyard. Dorchester 7.5 miles; Bridport 19.2 miles. (Ref. 1132007)

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


for 7 nights £433

Last booked 5 hours ago
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A living room with sofas and a pool table next to large windows with red curtains at Waterson in Osmington
30
Osmington, Dorset, DT3
  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.1★

    Good

  • Sykes rating

Semi-detached lovely holiday home perfect for families. Situated in Osmington Mills village. Garden. Welcomes two dogs. Shop 3 miles. Pub 2 miles. Beach 5 min. Weymouth 6 miles. (Ref. 994764)

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


for 7 nights £841

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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 £479

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A large brick house with white framed windows and a red roof surrounded by trees and bushes at Bayview Loft in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

A period conversion apartment Bayview Loft is located in an upmarket development in a highly desirable area of Weymouth in Dorset. Renovated early 2023. WiFi. (Ref. 1085793)

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


for 7 nights £501

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