Weymouth Holiday Cottages

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Your Weymouth, Dorset search returned 254 cottages

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A living room with a beige sectional sofa and colorful cushions a wicker coffee table a small round white table with baked goods a lamp a chair with a pillow a dining area with wooden chairs and a table at Winkle Cottage in Weymouth
Offer
38
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Winkle Cottage is a wonderful holiday home, set over three floors, situated in the popular coastal town of Weymouth in Dorset by the historic harbour. Dorchester 8.5 miles; Bridport 19.3 miles. (Ref. 1140944)

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

  • 10% off - Tue 1st Jul to 11th Oct 2025

7 nights from $818

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A brick two-story house with balconies and a hedge in front at Harbour Reach 6 in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A wonderful apartment that sleeps up to three people resting in Weymouth, Dorset. Open-plan. Near a beach. Close to amenities. Dorchester 7.8 miles; Bridport 18.5 miles. (Ref. 1057385)

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

7 nights from $617

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The exterior of a brick house with white doors and windows outdoor chairs and plants at Footprint Brewers Quay Harbour
22
Brewers Quay Harbour, Dorset, DT4
  • 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 $848

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Exterior of a building with wooden cladding black framed windows a black door benches and gravel at Overcombe Mill in Nottington near Weymouth
42
Nottington near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Overcombe Mill is a wonderful lodge nestled into the countryside of Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105455)

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

7 nights from $884

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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

7 nights from $753

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A living room with blue sofas a wooden coffee table and red rug by large windows overlooking the sea at Weymouth Bay in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4★

    Good

  • Sykes rating

A well-appointed apartment resting in Weymouth, Dorset. Stunning sea views. Open-plan living. Isle of Portland 7miles. Dorchester 7.8 miles. Bridport 21.5 miles. (Ref. 1003082)

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

7 nights from $875

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A brick house with white framed windows a pale green door and parking signs outside at Anchor Cottage in Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Anchor Cottage is a delightful, terraced home resting in the seaside town of Weymouth, Dorset. Close to a shop, a pub, and a beach. Family-friendly. Dorchester 7.6 miles; West Bay 17.8 miles. (Ref. 1150151)

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

7 nights from $728

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A living room with a TV on a white stand and a black sofa with animal print cushions at Sunny Days in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Modern refurbished terraced cottage in Weymouth, sleeping 4, short walk to the beach and town, WiFi, Off road parking for 1 car. (Ref. 994696)

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

7 nights from $693

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A street view showing the entrance door of Little Gull Cottage with steps and potted plants in Weymouth
21
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Little Gull Cottage is a lovely, three-storey holiday home close to Weymouth’s harbour in Dorset. Patio with furniture. Close to amenities. Smart TV. Dorchester 8.2 miles; Bridport 18.7 miles. (Ref. 1144645)

  • Wi-fi
  • Baby-friendly

7 nights from $726

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A brick house with a red door and white framed windows behind a stone wall at Weybury Cottage in Brewers Quay Harbour
18
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.3★

    Good

  • Sykes rating

A period three-storey terraced property resting in Weymouth, Dorset. In walking distance of amenities and beach. Pet-friendly. Isle of Portland 6.1 miles; Dorchester 8.7 miles. (Ref. 1055214)

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

7 nights from $832

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A brick terraced house with a green front door and front lawn at The Lookout -The House With A View in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4★

    Good

  • Sykes rating

A well-presented, mid-terrace property resting within the village of Wyke Regis. Sea views. Pet-friendly. WiFi. Weymouth 2 miles; Dorchester 9 miles. (Ref. 1006910)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $840

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A living room with a brown sectional sofa and decorative pillows a wooden coffee table with cups and a teapot two large windows with white shutters and a blue bean bag at Sunrise Apartment in Weymouth
36
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A contemporary first-floor apartment overlooking the coast in Weymouth, Dorset. Open-plan. Sea views. WiFi. Close to amenities. Dorchester 7.4 miles; Bridport 20.2 miles. (Ref. 1097676)

  • Wi-fi

7 nights from $740

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A brick house exterior with two white garage doors two upper windows and two front doors with canopies at Sea Pebbles in Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.0★

    Good

  • Sykes rating

Close to the harbour in Weymouth, Semi detached house, access to South West Coast path, WIFI, Close to shops, restaurants and café’s, suitable for families. (Ref. 994639)

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

7 nights from $952

Last booked 7 hours ago
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An outdoor area with a round hot tub surrounded by potted plants and a seating area with chairs and an umbrella at Kingeswic Cottage in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

This homely holiday cottage rests in Wyke Regis in Weymouth in Dorset. Pet-friendly. Nearby beach. Ideal for families. Isle of Portland 4.7 miles; Dorchester 9.4 miles; Bridport 18 miles. (Ref. 1050977)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Baby-friendly

7 nights from $930

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A brick semi detached house with a driveway garage and stairs leading to a gate at Dotties Retreat in Weymouth
46
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

  • Sykes rating

Dotties Retreat, a lovely, three-storey abode located in the seaside town of Weymouth, Dorset. Near beach. Off-road parking. Enclosed garden. Pet-friendly. Dorchester 8.7 miles; Bridport 18.8 miles. (Ref. 1157026)

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

7 nights from $896

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A row of colorful waterfront houses with windows and doors along a stone wall with wooden docks in front at Stanley House in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.3★

    Good

  • Sykes rating

Stanley House is an exceptional harbourside cottage located in the heart of Weymouth, Dorset. Sea views. Near amenities and beach. Near AONB. Stylish. Dorchester 8.4 miles; Bridport 19.9 miles. (Ref. 1138865)

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

7 nights from $1830

Last booked yesterday
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A building exterior with benches and gardens at Corvesgate Nottington near Weymouth
52
Nottington near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.0★

    Good

  • Sykes rating

Corvesgate is a tasteful property resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Shared garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105456)

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

7 nights from $842

Last booked 3 days ago
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A living room with two silver sofas a glass coffee table and two large windows at Royal Terrace View in Weymouth
23
Weymouth, Dorset, DT4
  • 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 $675

Last booked 2 days ago
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A front view of a large brick and white house with bay windows and a small porch at Dream View in Greenhill
24
Greenhill, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Located on the Esplanade in Weymouth with far reaching beach and sea views and within walking distance of the Harbour and town amenities. (Ref. 994167)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from $844

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A wooden building with multiple doors and windows with benches outside and gravel area in front at Egdon Heath in Nottington near Weymouth
46
Nottington near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

  • Sykes rating

Egdon Heath is a wonderful property resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105450)

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

7 nights from $918

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