Preston Holiday Cottages

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Preston Holiday Cottages

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Your Preston, Dorset search returned 399 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published
A view of buildings and beach at 32 Bowleaze Coveway in Preston
Offer New property
1 of 33
5
Preston, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

Bella Rosa a house in Preston, Dorset, boasts an en-suite bedroom, parking, beach views and proximity to Dorset's beaches and amenities. Weymouth 1 mile. (Ref. 1199281)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine

  • 10% off - Mon 13th Jul to 31st Dec 2026


for 7 nights From £517

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Exterior view of a stone house with white framed windows a white garage door and a small porch at Fisherbridge Cottage Weymouth
1 of 39
5
Weymouth, Dorset, DT3
  • Sleeps7
  • Bedrooms4
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

This pretty, detached cottage lies in Preston, Dorset. Smart TV. En-suite master bedroom. Close to amenities. Woodburning stove. Weymouth 3.6 mile. (Ref. 1119018)

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


for 7 nights From £661

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A garden with grass a wooden deck with a swing and a patio with chairs and a table at Blue Waters in Weymouth
1 of 25
5
Weymouth, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    5.0★

    Perfect

  • Sykes rating

A delightful, one-bedroom holiday home resting in Weymouth, Dorset. Contemporary. Private garden. Romantic. Close to amenities and beach. Near AONB. Open-plan. Dorchester 7 miles; Bridport 20.8 miles. (Ref. 1133982)

  • Wi-fi
  • Dishwasher


for 7 nights From £612

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A bungalow with a front yard at 7 Cedar Drive Preston
1 of 36
5
Preston, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    5.0★

    Perfect

  • Sykes rating

Cedar Drive is a charming house in Preston, Dorset, boasting ground-floor living, close proximity to local amenities and the coast for great days out. Weymouth 3.6 miles (Ref. 1173784)

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


for 7 nights From £508

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A garden with tables and chairs at Beck House in Weymouth
New property
1 of 28
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

Beck House, a welcoming mews house within a secure gated development in the heart of Weymouth, just a short walk from the harbour, beach and amenities. Dorchester 1.3 miles; Bridport 20.3 miles. (Ref. 1201741)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £515

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A dining table with flowers butter croissants orange juice and jam by windows overlooking a beach at Grandview in Weymouth
1 of 47
5
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

Easter Weekend open to book! A characterful first-floor apartment set on the Dorset coast, within the town of Weymouth. Outstanding sea views. Central location. Family-friendly. Isle of Portland 7 miles; Dorchester 7.2 miles; West Bay 18.1 miles. (Ref. 1049890)

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


for 7 nights From £835

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A row of brick terraced houses with bay windows and plants in front on a street at Seaside House in Weymouth
1 of 46
5
Weymouth, Dorset, DT4
  • Sleeps12
  • Bedrooms6
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

Elegant end of terrace Georgian Townhouse located in Weymouth. Close to amenities. Off-road parking. Pet-free. Courtyard with furniture. Dorchester 7.2 miles; Bridport 20.5 miles. (Ref. 1071940)

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


for 7 nights From £1180

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Rose Cottage - 1200211 - photo 1
1 of 60
5
Osmington, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

Rose Cottage, a charming thatched cottage nestled in Osmington, within Dorset National Landscape, boasts a large garden and proximity to local amenities. Weymouth 4.7 miles; Dorchester 7.9 miles; Poole 23.2 miles; (Ref. 1200211)

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


for 7 nights From £727

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The exterior entrance of a red brick building with blue door and blue trim around windows at Seasides in Weymouth
1 of 57
5
Weymouth, Dorset, DT4
  • Sleeps13
  • Bedrooms6
  • Pet FriendlyNo

    5.0★

    Perfect

  • Sykes rating

Lovingly renovated Seasides offers, beach, sea and harbour views, suitable for large family gatherings close to shops and amenities. (Ref. 1056791)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room
  • Sky TV


for 7 nights From £2111

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A living room with a sofa, chair, coffee table and television at 123 On The Sea – Victoria’s Place in Weymouth
New property
1 of 30
5
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

  • Sykes rating

123 On The Sea – Victoria’s Place is a beautifully appointed seafront apartment in Weymouth, Dorset, featuring beach views, private parking, and a bright open-plan layout. Dorchester 7.6 miles; Bridport 21.2 miles. (Ref. 1133962)

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


for 7 nights From £571

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A small blue house with patio furniture and potted plants on a tiled patio at Outlook Lodge in Bowleaze
1 of 28
5
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    5.0★

    Perfect

  • Sykes rating

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

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


for 7 nights From £762

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A bungalow with a tiled roof and gravel front garden with plants at The Willows in Preston Weymouth
1 of 31
5
Preston, Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    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 From £625

Last booked yesterday
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Front exterior of a brick house with white-framed windows and door and garden shrubs with black chairs and table outside at Splash in Weymouth
1 of 22
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

Splash, a lovely, terrace cottage lies in the heart of Weymouth, a seaside town in Dorset. Near beach and pub. Smart TV. Near harbour. Dishwasher. Dorchester 8.6 miles; Bridport 19.4 miles. (Ref. 1154894)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights From £684

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A house with a thatched roof and stone walls at Woodbine Cottage in Weymouth
New property
1 of 57
5
Osmington, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

  • Sykes rating

Woodbine Cottage is a welcoming holiday home in Weymouth, Dorset, boasting a woodburning stove, enclosed rear patio and easy access to local amenities. Weymouth 4.7 miles. (Ref. 1203009)

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


for 7 nights From £718

Last booked yesterday
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A brick building with multiple bay windows and doors along a street at The BoBo House in Weymouth
1 of 56
5
Weymouth, Dorset, DT4
  • Sleeps12
  • Bedrooms6
  • Pet FriendlyNo

    5.0★

    Perfect

  • Sykes rating

The BoBo House is a delightful terraced holiday home resting in the popular coastal town of Weymouth in Dorset set over four floors and near the beach. Dorchester 7 miles; Bridport 17 miles. (Ref. 1059621)

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


for 7 nights From £1073

Last booked yesterday
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A stone building facade with multiple windows flower boxes and a wrought iron fence at The Esplanade in Weymouth
1 of 85
5
Weymouth, Dorset, DT4
  • Sleeps18
  • Bedrooms9
  • Pet FriendlyNo

    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 From £2519

Last booked yesterday
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The exterior of a modern house with curved walls dark framed windows a paved pathway and garden beds at Flat 2 38 Preston Road Weymouth
1 of 27
5
Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

This spacious ground-floor apartment is nestled in the gorgeous seaside town of Weymouth in Dorset. Bike/kayak storage. En-suite. WiFi. Dorchester 6.3 miles; Isle of Portland 8.6 miles; West Lulworth 12.3 miles. (Ref. 1037083)

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


for 7 nights From £475

Last booked yesterday
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A two-story corner house with a pink brick exterior and a bay window at Mermaid House in Brewers Quay Harbour
1 of 41
5
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

This stylish and neat holiday home rests in Brewers Quay Harbour in Weymouth, Dorset. Close to amenities and harbour. Pet-free. Garden. Dorchester 8.7 miles; West Lulworth 15.8 miles. (Ref. 1093760)

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


for 7 nights From £619

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A garden with seating area and conservatory at Honeypot Cottage in Weymouth
New property
1 of 24
5
Preston, Dorset, DT3
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

  • Sykes rating

A traditional, thatched cottage resting within the village of Preston. WiFi. Pub and shop within 0.1 miles. Weymouth 3.5 miles. (Ref. 1201976)

  • Wi-fi
  • Washing machine


for 7 nights From £537

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A corner seating area with two black armchairs near bay windows and a side table with a lamp at Two @ No36 in Weymouth
1 of 31
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

Two @ No36, a wonderful, first-floor apartment situated in the heart of Weymouth in Dorset, with the beach on your doorstep. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162203)

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


for 7 nights From £736

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Map View

Please find below a selection of self catering holiday cottages to rent in or near Preston.

And if you fancy a classic seaside experience, head to Blackpool and Cleveleys, where you can enjoy beaches, promenades, and plenty of family attractions.