Preston Holiday Cottages

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Your Preston, Dorset search returned 376 cottages

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Front of a white building with black door and window frames flowers in front at Harbour Reach Brewers Quay Harbour
36
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

Stylish fisherman’s cottage just a few minutes’ walk from Old Harbour in Weymouth. Beach 1 mile. Harbour, shop and pub 5 min. Welcomes one dog. Poole 33 miles. (Ref. 1058438)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $754

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A living room with a blue sofa and ottoman near a fireplace and television at Owls Rest in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A homely, mid-terrace cottage based in Weymouth. Enclosed decking. Smart TV. Beach nearby. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1094925)

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


for 7 nights $738

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A stone building facade with multiple windows flower boxes and a wrought iron fence at The Esplanade in Weymouth
85
Weymouth, Dorset, DT4
  • Sleeps18
  • Bedrooms9
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

The Esplanade is a stunning, nine-bedroom holiday dwelling residing in Weymouth, Dorset. Sea views. En-suite bedrooms. Close to amenities and a beach. Parking. Dorchester 7.2 miles; Bridport 18.7 miles. (Ref. 1123341)

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


for 7 nights $3404

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A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
18
Upwey, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

This picturesque cottage, situated in the village of Upwey, with parking. Short drive to Weymouth. Close to pub and tea rooms. Lovely walks nearby. (Ref. 994658)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights $631

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A bungalow with a tiled roof and gravel front garden with plants at The Willows in Preston Weymouth
29
Preston, Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

This delightful, two-bedroom bungalow rests in Preston, Dorset. Ground-floor living. Enclosed garden. Near an AONB. Weymouth 3.5 miles. (Ref. 1126160)

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


for 7 nights $793

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A harbor with boats docked near buildings and a raised drawbridge at Harbours Edge in Brewers Quay Harbour
27
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.1★

    Good

  • Sykes rating

Perfectly located on the harbour side in the heart of Weymouth. Watch the boats sail by and the daily catch being landed. (Ref. 994172)

  • Wi-fi
  • Washing machine


for 7 nights $738

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A street view of brick terraced houses with windows and front doors under a blue sky at Victoria House in Weymouth
37
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Victoria House is a pleasant holiday home resting in the coastal town of Weymouth in Dorset. Public car parking. Over three floors. Near amenities. Dorchester 8 miles; Bridport 20.2 miles. (Ref. 1148491)

  • Wi-fi


for 7 nights $618

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A brick terraced house with a white front door gravel front garden and small plants at Home Waters in Wyke Regis
23
Wyke Regis, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Off road parking. Sleeping 6 close to Portland marina. Dog friendly. (Ref. 994270)

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


for 7 nights $738

Last booked today
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A small dining area with a round glass table set for two and wicker chairs by two windows with ocean views at 6 The Beaches in Weymouth
16
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.6★

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

A modern studio apartment on the seafront on Weymouth, Dorset. Open-plan living. Sea views. Perfect for couples. (Ref. 1003545)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $561

Last booked 2 days ago
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An old stone building with multiple gables and windows behind a stone wall at The Old Portland Courthouse in Portland
33
Portland, Dorset, DT5
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.2★

    Good

  • Sykes rating

The Old Portland Courthouse is spacious, comfortable luxury holiday home. Sleeps 8 people. Wifi. Pub and shop 10 min. Beach 5 min. Weymouth 5 miles. (Ref. 994487)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights $1557

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A garden with flowers a wooden arch and a raised deck attached to a brick house at Little Retreat in Upwey
21
Upwey, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Village pubs and tea rooms. Sleeps two. Parking for one car. 10 mins from Weymouth. Patio and garden. (Ref. 994358)

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


for 7 nights $644

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A glass table with sunglasses fruit bowl champagne bottle and glasses overlooking a beach and sea at 123 On The Sea in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

123 On The Sea is a lovely, two-bedroom apartment residing in Weymouth, Dorset. Near Dorset AONB. Sea views. Close to amenities and a beach. Private balcony. Off road parking. Dorchester 7.3 miles; Bridport 18.9 miles. (Ref. 1133961)

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


for 7 nights $682

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A balcony with a round table holding a bottle and two wine glasses with two chairs and a sea view at Sunbeach in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A neat, first-floor apartment set overlooking the Pavillion on Weymouth seafront. Excellent location. Smart TV. WiFi. Dorchester 7.4 miles; Bridport 18.8 miles. (Ref. 1123724)

  • Wi-fi


for 7 nights $725

Last booked 4 hours ago
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An exterior view of Shepherd Oak near Weymouth with plants and a wooden wall
51
Upwey near Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4★

    Good

  • Sykes rating

Stunning semi-detached holiday cottage in courtyard setting, on the edge of Upwey, near Weymouth. Very high standard of accommodation with en-suite facilities and vaulted ceiling. Dog-friendly, plenty to see and do in the area. Weymouth 3.5 miles. (Ref. 932158)

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


for 7 nights $802

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A row of attached houses with brick and beige facades on a street with sidewalks at Globe Cottage in Weymouth
27
Weymouth, Dorset, DT4
  • Sleeps7
  • Bedrooms3
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Three bedroom terraced property in central Weymouth. Open plan living area. (Ref. 1095056)

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


for 7 nights $956

Last booked yesterday
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An outdoor balcony with a table set with plates cups a teapot and pastries with buildings in the background at Spindrift Brewers Quay Harbour
38
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms4
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Spindrift is a characterful, home resting upon Brewers Quay Harbour in Dorset. Original features. Close to amenities, attractions and the harbour. Balcony. Dorchester 8.5 miles; West Lulworth 15.3 miles. (Ref. 1137640)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights $838

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A brick house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
24
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Situated in a gated complex near Weymouth harbour. WiFi. Parking. Close to bars and restaurants. (Ref. 994560)

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


for 7 nights $758

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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

    4.8★

    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 $899

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Stone goose sculpture on grass with white buildings and a lighthouse tower in the background at Old Higher Lighthouse Stopes Cottage in Portland Bill
55
Portland Bill, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic Coast. Amazing views. Shared access to lighthouse observatory. Shared use of seasonal outdoor heated pool and Jacuzzi. (Ref. 12494)

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


for 7 nights $946

Last booked 2 days ago
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A single-story building with mixed stone and brick walls a green door and multiple windows beside a gravel pathway and picnic table at Hebe in Notton near Maiden Newton
34
Notton near Maiden Newton, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A delightful, two-bedroom barn conversion resting in Notton, Dorset. Disabled-friendly. Dog-friendly. Eco-friendly. Enclosed garden. West Bay 15 miles; Weymouth 16.2 miles; Lyme Regis 24 miles. (Ref. 1096950)

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


for 7 nights $966

Last booked 2 hours ago
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