Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 345 cottages

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A row of attached houses with one blue house covered in climbing plants and flowers in front at Fenders Brewers Quay Harbour
30
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

Delightful terraced cottage. Central Weymouth location. Close to Harbour and beach . sleeping 4. Enclosed garden. WiFi. Weymouth beach just 10 minutes away. (Ref. 998253)

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

7 nights from £567

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The front exterior of a row of brick terraced houses with bay windows and small brick walls at Southview Retreat in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Attractive terraced house situated in Weymouth, wonderfully modernised. Off-road parking. WiFi. Beach 1 mile. Pet-friendly. Dorchester 7 miles; Bridport 17 miles. (Ref. 1010311)

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

7 nights from £848

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A rocky shoreline with a small beach a stone wall and garden plants at Weymouth Bay Apartment A in Weymouth
49
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A lovely two-bedroom, ground-floor apartment resting in Weymouth, Dorset. Near a beach. Close to amenities. Romantic. Ground-floor. Dorchester 7.5 miles; Bridport 20.5 miles. (Ref. 1083146)

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

7 nights from £649

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A row of houses with white and blue walls and small gardens along a brick pathway at Little Tern Brewers Quay Harbour
31
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A delightful, mid-terrace cottage resting in Brewers Quay Harbour, Dorset. Designated parking. Pet-friendly. Enclosed garden. Weymouth 0.6 miles; Dorchester 8.8 miles; West Lulworth 15.7 miles. (Ref. 1084006)

  • Dishwasher
  • Washing machine

7 nights from £579

Last booked yesterday
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An outdoor area with a round hot tub surrounded by potted plants and a seating area with chairs and an umbrella at Kingeswic Cottage in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

This homely holiday cottage rests in Wyke Regis in Weymouth in Dorset. Pet-friendly. Nearby beach. Ideal for families. Isle of Portland 4.7 miles; Dorchester 9.4 miles; Bridport 18 miles. (Ref. 1050977)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Baby-friendly

7 nights from £698

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The exterior of a white terraced house with blue doors and window sills at South Harbour Cottage in Weymouth
17
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3★

    Good

  • Sykes rating

A pretty, renovated terraced cottage, close to the old harbour and Brewers Quay in Weymouth. WiFi. Pet-friendly. Close to beach. Dorchester 8.4 miles; Bridport 19.2 miles. (Ref. 1043009)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £552

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A row of yellow terraced houses with street lamps and paved walkways at Olympic Cottage in Portland
23
Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

Modern and spacious cottage for couples or family in the Isle of Portland. Enclosed garden. Welcomes one dog. Pub and shop 10 min. Beach 5 min. Weymouth 5 miles. (Ref. 994497)

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

7 nights from £595

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A row of terraced houses with flowers and bushes in front and a view of the sea at Langham Cottage in Portland
35
Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. Accepts one dog. Pub and shop 5 min. Beach 5 min. Bridport 23 miles. (Ref. 994321)

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

7 nights from £462

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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

    4.3★

    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

7 nights from £566

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A brick front house with a white door black door windows a bench and a paved driveway at Jay Cottage in Weymouth
37
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A lovely terraced house resting in a quiet residential area of Weymouth, Dorset. Enclosed garden. Pet-friendly. Near to beach. Dorchester 10.1 miles; Bridport 18.8 miles. (Ref. 1053611)

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

7 nights from £468

Last booked yesterday
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A living room with two blue sofas and a wooden coffee table next to a fireplace and dining area in the background at Day Cottage in Weymouth
Offer
40
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A delightful, terraced cottage nestled into the coastal town of Weymouth, Dorset. Open-plan living. Near amenities and beach. Close to attractions. Pet-friendly. Dorchester 8.4 miles; West Bay 18 miles; Lyme Regis 32.6 miles. (Ref. 1124105)

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

  • 10% off - Tue 24th Jun to 2nd Aug 2025

7 nights from £452

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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

7 nights from £503

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A street view of terraced houses with one painted blue and windows and doors visible at Mackerel Cottage in Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2★

    Good

  • Sykes rating

Mackerel Cottage is a beautifully-designed, terrace cottage resting in the heart of Weymouth, Dorset. Woodburning stove. Pet-friendly. Near shop and pub. Dorchester 8.4 miles; Bridport 18.9 miles. (Ref. 1141828)

  • Wi-fi
  • Dishwasher

7 nights from £506

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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
  • PetsYes

    4.2★

    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

7 nights from £635

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A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. Designated parking. Close to a beach and amenities. Enclosed garden. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1133998)

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

7 nights from £653

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The front exterior of a red brick house with white framed windows and a white front door at 74 Reap Lane Southwell near Weston
30
Southwell near Weston, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2★

    Good

  • Sykes rating

74 Reap Lane is a lovely home resting near the village of Weston, on the Isle of Portland in Dorset. Near beach and pub. Pet-friendly. Off-road parking. Fortuneswell 2.2 miles; Weymouth 7.8 miles; Dorchester 14.8 miles. (Ref. 1158199)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £471

Last booked 2 days ago
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A living room with a brown leather sofa blue armchair glass coffee table and television at Tides Corner in Bowleaze
36
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A modern ground floor annex in Weymouth, just moments from the beach. 1 well behaved pet, WiFi, parking for two cars. (Ref. 994726)

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

7 nights from £714

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A small blue house with patio furniture and potted plants on a tiled patio at Outlook Lodge in Bowleaze
28
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A lodge sleeping four people, Bowleaze area of Weymouth. Dog friendly. Large garden. Parking for two cars. (Ref. 994500)

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

7 nights from £783

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An outdoor dining area with a table and six chairs set in front of a bunker entrance with grass on the roof at The Transmitter Bunker in Ringstead
33
Ringstead, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

This quirky, converted bunker rests in Ringstead near Preston, Dorset. Open fire. In an AONB. Smart TV. Off-road parking. Weymouth 7.6 mile. (Ref. 1131689)

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

7 nights from £824

Last booked 2 days ago
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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

    4.3★

    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

7 nights from £499

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