Chiswell On Portland Holiday Cottages

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Your Portland, Dorset search returned 353 cottages

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The Old Post Office - 1127439 - photo 1
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

The Old Post Office, a stylish pet-friendly house nestled in the town Weymouth, Dorset, features a Smart TV, proximity to the beach and marina. Dorchester 8.5 miles; Bridport 20.5 miles. (Ref. 1127439)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £517

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Harbour Reach 7 - 1194446 - photo 1
New property
26
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Harbour Reach 7, an agreeable second-floor apartment in the town of Weymouth, in Dorset, boasts proximity to the beach, shop and pub and West Dorset Heritage Coast. Dorchester 7.9 miles; Bridport 18.5 miles. (Ref. 1194446)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £653

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An exterior view of a house with steps and a blue door at Corner Cottage in Preston
Offer
31
Weymouth, Dorset, DT3
  • Sleeps5
  • Bedrooms3
  • PetsNo

  • Sykes rating

Ash Corner Cottage is a lovely house in Preston near Weymouth Dorset, with sea views from the bedrooms, an enclosed multi-level garden and is a 20 minute walk or short drive to the beach. Weymouth 3.8 miles. (Ref. 1176572)

  • Wi-fi
  • Off-road parking
  • Dishwasher

  • 5% off - Wed 25th Mar to 18th Jul 2026


for 7 nights £693

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Two small wooden cabins in a grassy area with trees and outdoor wooden table and chairs with red flowers at Fallow in Warmwell
22
Warmwell, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Fallow is a superb hut near Broadmayne, Dorset, boasting impressive countryside views to admire with the fire pit in the garden and a woodburning stove. Dorchester 5.8 miles; Weymouth 8.2 miles; Bridport 20.6 miles; Swanage 21 miles. (Ref. 1174455)

  • Off-road parking
  • Ground floor bedroom


for 7 nights £367

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A house with white facade and windows at NO 10 Fortuneswell
New property
34
Fortuneswell, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

NO 10 is a fine, dog-friendly house situated in Fortuneswell, Dorset, featuring an electric fire, an enclosed courtyard, and easy access to the beach. Weymouth 5.1 miles. (Ref. 1200066)

  • Wi-fi
  • Dishwasher


for 7 nights £620

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A building exterior with balcony and entrance at Portland View in Portland Bill
New property
21
Portland Bill, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

A beautifully presented apartment with stunning views across the bay and Portland Bill. Open-plan living. WiFi. Scenic views. Weymouth 7.8 miles. (Ref. 1201975)

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


for 7 nights £557

Last booked 2 days ago
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A living room with a dining area and furniture at Home from Home near the Sea Weymouth
New property
40
Wyke Regis, Dorset, DT4
  • Sleeps8
  • Bedrooms4
  • PetsNo

  • Sykes rating

Home from Home near the Sea is a neat three-storey house resting in Wyke Regis, Dorset, featuring easy access to the beach and nearby local amenities. Weymouth 2.8 miles; Dorchester 10.2 miles. (Ref. 1200131)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights £884

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A front entrance with a blue door and window at 23 The Maltings in Weymouth
New property
27
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Dolphin Cottage is a lovely cottage nestled into the bustling seaside town of Weymouth, Dorset, close to a shop, pub, local walks, and beaches. Fortuneswell 4.8 miles; Dorchester 8.9 miles; Bridport 19.5 miles. (Ref. 1179916)

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


for 7 nights £659

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A living room with a dining table and kitchen appliances at Rodwell Holt in Weymouth
New property
29
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Rodwell Holt, a pleasing first-floor apartment in Weymouth, Dorset, features a balcony and offers easy access to the harbour, beach, and local amenities. Dorchester 8.1 miles; Bridport 21.5 miles. (Ref. 1191754)

  • Wi-fi
  • Dishwasher


for 7 nights £564

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An exterior of a property showcasing a door and windows at 46 Chafeys Avenue
New property
45
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

  • Sykes rating

Wilkie's Place is a welcoming, pet-friendly house near the beach in Weymouth, Dorset, featuring a conservatory and an enclosed, multi-tiered garden. Dorchester 7.5 miles; Bridport 18.8 miles. (Ref. 1196651)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine


for 7 nights £999

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A house with windows and garden at 15 Coombe Avenue
New property
28
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

  • Sykes rating

15 Coombe Avenue is a welcoming, pet-friendly house near the beach in Weymouth, Dorset, with driveway parking, a conservatory, and ground-floor living. Dorchester 6.9 miles; Bridport 20.5 miles. (Ref. 1194203)

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


for 7 nights £773

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A house with a garage and plants in front at Millmead House Annex Portesham
New property
27
Portesham, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Millmead House Annex is a welcoming holiday annex in Portesham, Dorset, featuring open‑plan living, a woodburning stove and an enclosed garden. Weymouth 7.8 miles; Dorchester 7.8 miles (Ref. 1201417)

  • Wi-fi
  • Off-road parking


for 7 nights £437

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A house with garage and pathway at Millmead House in Portesham
New property
61
Portesham, Dorset, DT3
  • Sleeps8
  • Bedrooms4
  • PetsYes

  • Sykes rating

Millmead House is a welcoming house in Portesham, Dorset, within the Dorset National Landscape, featuring a toasty woodburning stove and a garden. Weymouth 7.8 miles; Dorchester 8.1 miles (Ref. 1200773)

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


for 7 nights £1121

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