Preston Holiday Cottages

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Preston Holiday Cottages

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Your Preston, Dorset search returned 398 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 garden with grass a wooden deck with a swing and a patio with chairs and a table at Blue Waters in Weymouth
Offer
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

  • £41 off - Fri 7th Aug to 28th Aug 2026


for 7 nights From £692

Last booked 2 days ago
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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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Rose Cottage - 1200211 - photo 1
New property
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 £718

Last booked yesterday
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An outdoor patio area with a wooden table and six wooden chairs in front of a modern concrete structure with large sliding glass doors at Standby Generator Bunker Ringstead near Weymouth
1 of 68
5
Ringstead near Weymouth, Dorset, DT2
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

Standby Generator Bunker, an impressive abode, rests in rural Ringstead in Dorset, enjoying sea views, a pet-friendly policy, and a woodburning stove. Dorchester 8.3 miles; Bridport 23.1 miles. (Ref. 1137374)

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


for 7 nights From £989

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A living room with a sofa and dining table at Red Rose Apartment in Weymouth
1 of 22
5
Weymouth, Dorset, DT4
  • Sleeps3
  • Bedrooms1
  • Pet FriendlyNo

  • Sykes rating

Red Rose Apartment is a centrally located apartment resting in Weymouth, Dorset and boasts parking, sea views and is within walking distance of the beach. Dorchester 7.8 miles; Bridport 19 miles. (Ref. 1190887)

  • Wi-fi
  • Washing machine


for 7 nights From £665

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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 £519

Last booked yesterday
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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 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 £638

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A wooden front door next to a window with shutters and a gray mailbox numbered 20 at Smugglers Cottage in Weymouth
1 of 27
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

A contemporary, three-storey property resting by the harbour in Weymouth, Dorset. Gas Fire in Lounge, WiFi. Close to beach and amenities. Weymouth 1 mile; Dorchester 8.6 miles. (Ref. 1058500)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £644

Last booked yesterday
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An outdoor garden area with a gravel path picnic table plastic chairs and trees at Riverhouse Lodge in Upwey
Offer
1 of 21
5
Upwey, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6★

    Outstanding

  • Sykes rating

A pretty village lodge, close to the seaside town of Weymouth in Dorset. Traditional. Beautiful Mediterranean-style garden. WiFi. Dorset AONB. Dorchester 4.9 miles. (Ref. 1017591)

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

  • 15% off - Sat 11th Jul to 5th Sep 2026


for 7 nights From £385

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A living room with a grey sofa with colorful cushions a glass coffee table and a fireplace at Ocean Retreat in Weymouth
1 of 14
5
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

A stylish and contemporary apartment set in the town of Weymouth, Dorset. Seaside setting. Fantastic views. Off-road parking. Fortuneswell 5.8 miles; Dorchester 7.2 miles; Bridport 20.9 miles. (Ref. 1072234)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £773

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A brick house with white framed windows and door with two black chairs and a small table outside at Nuke in Weymouth
1 of 22
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

This cottage boast style, character, and a fabulously contemporary interior. Central location. Surrounded by history. WiFi. Rodwell 0.9 miles. (Ref. 1005313)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £672

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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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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

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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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The exterior of a house with white walls and wooden paneling a patio area with a table umbrella and chairs at Whitegates Lodge in Osmington
1 of 15
5
Osmington, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

Link detached modern annex lodge in the Dorset Coastal village of Osmington. Wifi. Parking for two cars. Short drive to Weymouth. (Ref. 994794)

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


for 7 nights From £944

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A marina with boats and yachts docked and buildings in the background at Harbourside Haven Apartment 1 in Weymouth
1 of 18
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

A superb first-floor apartment resting in Weymouth, Dorest. Stunning marina views. Allocated off-road parking. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059262)

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


for 7 nights From £620

Last booked 2 days ago
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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

Last booked yesterday
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A living room with two grey sofas and a wooden boat-shaped shelf with books at Chesil Retreat Weymouth
1 of 32
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

A stylish property resting in the resort of Weymouth, Dorset. Enclosed garden. Pet free. Beach nearby. Dorchester 10.1 miles; Bridport 18.8 miles. (Ref. 1100742)

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


for 7 nights From £510

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A living room with leather sofas glass coffee table and a television near large windows overlooking boats at Harbourside Haven Apartment 4 in Weymouth
1 of 20
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6★

    Outstanding

  • Sykes rating

A stylish and contemporary apartment overlooking Weymouth Harbour in Dorset. Balcony. Underfloor heating. Smart TV. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059265)

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


for 7 nights From £629

Last booked yesterday
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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.