Preston Holiday Cottages

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Preston Holiday Cottages

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

Last booked yesterday
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A living room with two sofas a coffee table a TV and paintings on the wall at Harbour Watch 2 in Weymouth
1 of 18
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.3★

    Good

  • Sykes rating

Located on the harbourside, is this two-bedroom contemporary apartment in Weymouth, Dorset. WiFi. Fortuneswell 4.7 miles; Dorchester 9.3 miles. (Ref. 1017563)

  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights From £832

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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 £519

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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

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 living room with a sofa, chair, coffee table and television at 123 On The Sea – Victoria’s Place in Weymouth
New property
1 of 32
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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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 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 window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour
1 of 45
5
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1107011)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £485

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 £1022

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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 row of colorful terraced houses with blue cream pink and white facades on a cobblestone street at Harbour Tales in Weymouth
1 of 38
5
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

A beautiful terraced fisherman’s cottage resting in the coastal town of Weymouth, Dorset. Close to a beach. Close to a pub. TV. Dorchester 8.4 miles; West Bay 18.1 miles, Lyme Regis 32.6 miles. (Ref. 1133009)

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


for 7 nights From £604

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An outdoor garden area with a gravel path picnic table plastic chairs and trees at Riverhouse Lodge in Upwey
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


for 7 nights From £385

Last booked yesterday
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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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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 2 days ago
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A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
1 of 31
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. Designated parking. Close to a beach and amenities. Enclosed garden. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1133998)

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


for 7 nights From £602

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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

Last booked 2 days ago
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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

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

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.