Preston Holiday Cottages

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Your Preston, Dorset search returned 376 cottages

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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

An attractive, converted Victorian school resting within Piddletrenthide. WiFi. Woodburning stove. Pet-friendly. Off-road parking. Dorchester 8 miles. (Ref. 933650)

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

7 nights from $780

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Modern and comfortable holiday house for up to 8 people in the Isle of Portland. Enclosed garden with patio. Pub and shop 5 min. Beach 5 min. Weymouth 5 miles. (Ref. 994310)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Sat 6th Sep to 20th Dec 2025

7 nights from $1233

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This seafront, second-floor apartment sits in Weymouth, Dorset. Pay and Display parking nearby. Romantic. Sea views. Open-plan. Pet-free. Dorchester 7.6 miles; Bridport 20.3 miles. (Ref. 1107825)

  • Wi-fi

7 nights from $678

Last booked 3 hours ago
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8

    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 $713

  • 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 $754

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.3

    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 $820

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

Delightful stone terraced cottage close to Old Harbour in Weymouth, Dorset. Conservatory and garden. Pet-friendly. Beach 1 mile, shop and pub 0.3 miles. Dorchester 7 miles. (Ref. 1000703)

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

7 nights from $773

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.3

    Good

  • Sykes rating

A well-positioned, three-storey home resting in Weymouth, Dorset. Close to amenities, harbour, and the beach. Family-friendly. Stylish. Elevated terrace. Central. Dorchester 8.4 miles; Bridport 18.5 miles. (Ref. 1122030)

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

7 nights from $817

  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

The Cheesehouse is an exceptional, pet-friendly five-bedroom home resting in Litton Cheney, Dorset featuring a games room with pool, darts and bar area. Dorchester 9.9 miles; Yeovil 20.9 miles. (Ref. 1161994)

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

7 nights from $1972

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Footprint a converted stable located in a gated development in Weymouth close to harbour and beach. En-suite master bedroom. Beach 1 mile. Dorchester 9 miles. (Ref. 994201)

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

7 nights from $830

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.2

    Good

  • Sykes rating

The Lobster Pot, a nicely-presented apartment rests in the gorgeous seaside town of Weymouth in Dorset. Open plan. En-suite. Close to beach and amenities. Dorchester 8.7 miles; Bridport 20.4 miles. (Ref. 1151706)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from $626

  • Sleeps4
  • Bedrooms3
  • PetsNo

    4.3

    Good

  • Sykes rating

A wonderful holiday home resting on the outskirts of Portesham, Dorset. Countryside views. Open-plan living. Barbecue. Decking. Weymouth 8 miles; Dorchester 8 miles. (Ref. 1127855)

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

7 nights from $529

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.2

    Good

  • Sykes rating

A well-presented, modern apartment on the rugged Isle of Portland. Far reaching sea views. Open plan living. Balcony with seating. Access to indoor swimming pool and gym. Close to pub, beach and shop. WIFI and allocated parking. Weymouth within 6 miles. (Ref. 1034885)

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

7 nights from $722

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    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 $717

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A charming townhouse set over three floors in the centre of Dorchester. Character features. Off-road parking. Central town location. Weymouth 8.8 miles. (Ref. 1077743)

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

7 nights from $1083

Last booked 4 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

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

7 nights from $828

Last booked 4 hours ago
See more details
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3

    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 $624

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3

    Good

  • Sykes rating

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

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

7 nights from $814

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.1

    Good

  • Sykes rating

Three bedroomed bungalow located just half a mile from Ringstead Beach. A large garden, welcomes 2 dogs, a good base for walking the coast path. (Ref. 994807)

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

7 nights from $711

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.3

    Good

  • Sykes rating

A contemporary three-storey holiday home settled in the heart of Weymouth, Dorset. Enclosed courtyard. Close to the beach. Pet-free. Dorchester 7.9 miles; Bridport 20.1 miles. (Ref. 1088903)

  • Wi-fi
  • Dishwasher

7 nights from $992