Weymouth Holiday Cottages

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Your Weymouth, Dorset search returned 261 cottages

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A stone building with a conical roof and blue chimney pipes next to brick and blue wooden sections at The Oast House in Brewers Quay Harbour
49
Brewers Quay Harbour, Dorset, DT4
  • Sleeps10
  • Bedrooms4
  • PetsNo

    4.4★

    Good

  • Sykes rating

Electronically gated property. Gated parking for three cars. Sleeps 10. Two min walk to harbour and amenities. (Ref. 994443)

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


for 7 nights $1846

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A brick exterior with white doors windows hanging plants and a sculpture at Barley Mews Brewers Quay Harbour
50
Brewers Quay Harbour, Dorset, DT4
  • Sleeps9
  • Bedrooms4
  • PetsNo

    4.3★

    Good

  • Sykes rating

A beautiful conversion of the Devenish Brewery malthouse, just moments from the harbourside. Sleeps 9, WIFI, stylish curved kitchen. Games Room (Ref. 993976)

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


for 7 nights $1635

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Front view of a brick house with decorated windows and a black door with red steps and a driveway at Gone Fishing in Brewers Quay Harbour
32
Brewers Quay Harbour, Dorset, DT4
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Four bedroom semi-detached property in Weymouth. WiFi. Off road parking two cars. Large patio. (Ref. 994226)

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


for 7 nights $1294

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A beachfront with a stone barrier green garden and a small gate at Weymouth Bay Apartment C in Greenhill
19
Greenhill, Dorset, DT4
  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Second floor comfy apartment sleeping 7 guests close to the sea in Weymouth. Welcomes two dogs. Garden. Beach 2 min. Shop 10 min. Pub 5 min. Dorchester 7.6 miles. (Ref. 994773)

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


for 7 nights $763

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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

    4.6★

    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


for 7 nights $733

Last booked yesterday
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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


for 7 nights $672

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A living room with a blue armchair a colorful armchair a television a small fireplace and blue curtains at The Skipper's House in Weymouth
36
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

A delightful, three bed property nestled in the heart of Weymouth, Dorset. Enclosed courtyard. Washing machine. Smart TV. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1132346)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $625

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A street view of brick buildings including Bay View Hotel and a pop-up pizza shop at The Loft @ No36 in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

The Loft @ No36, a contemporary, third-floor apartment situated in the heart of Weymouth in Dorset, enjoying sea views with the beach on your doorstep. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162205)

  • Wi-fi
  • Off-road parking


for 7 nights $745

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An outdoor view of a brick building with windows and a door at Mutiny House, Brewers Quay Harbour
31
Brewers Quay Harbour, Dorset, DT4
  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.3★

    Good

  • Sykes rating

Mutiny House is situated in a harbourside location in Weymouth. Perfect for a family or group of friends. WiFi. Pub and shop 1 min. Beach 0.5 mile. Dorchester 8.5 miles. (Ref. 994414)

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


for 7 nights $927

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A two story detached house with bay windows and a central front door with plants on each side at Family House in Weymouth
46
Weymouth, Dorset, DT3
  • Sleeps12
  • Bedrooms6
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

A spacious, detached, three-storey house nestled in Weymouth, Dorset. Close to amenities. Close to beach. Pet-free. Enclosed garden. Dorchester 6.5 miles; Bridport 18 miles. (Ref. 1080182)

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


for 7 nights $1761

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Terraced houses with bay windows and colored doors on a street at 26 High West in Weymouth
27
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2★

    Good

  • Sykes rating

26 High West is a beautifully-presented townhouse located near the harbour in the lovely town of Weymouth, Dorset. Pet-friendly. Near beach. Electric fire. Dorchester 8.2 miles; Bridport 18.9 miles. (Ref. 1135362)

  • Wi-fi
  • Dishwasher


for 7 nights $633

Last booked yesterday
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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

    4.7★

    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 $869

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A living room with a blue sofa and television at Saddlers Cottage in Weymouth
17
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

A well-positioned, two-bedroom home resting in Weymouth, Dorset. Close to amenities, attractions and beach. Pet-friendly. Near AONB. Enclosed small courtyard. Dorchester 7.5 miles; Bridport 19.2 miles. (Ref. 1132007)

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

  • $43 off - Sat 14th Mar to 21st Mar 2026


for 7 nights $568

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Exterior view of a white house with flower pots near the door and a tree in the foreground at The Little Cottage in Weymouth
27
Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A quaint, white-washed cottage resting in Weymouth, Dorset. Off-road parking. Smart TV. Open-plan living. Xbox. Close to beach. Dorchester 5.2 miles; Bridport 17 miles; Lyme Regis 26.3 miles. (Ref. 1113457)

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


for 7 nights $757

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An outdoor area with a wooden building and gravel pathway at Dirdale in Weymouth
45
Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Dirdale is a tasteful lodge resting in rural 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. 1105458)

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


for 7 nights $902

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A blue building with bay windows and two white doors behind a black metal fence at Brewers Quay Harbour
23
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

All second floor. Two bedrooms: 1 x double bed with en-suite shower, basin and WC, 1 x twin single. Bathroom with bath, basin and WC. Open plan living area with kitchen, dining area and sitting area. (Ref. 994293)

  • Wi-fi


for 7 nights $877

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A driveway leading to a single-story brick house with a red door and a small front lawn at Sunny Haven in Preston
26
Preston, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A lovely two-bedroom bungalow resting in Preston, Dorset. Dog-friendly. Off-road parking. Private garden. Close to amenities. Weymouth 3.4 mile. (Ref. 1106680)

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


for 7 nights $806

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A stone building with white framed windows and a door along a paved street in a residential area at Brewers Retreat in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.4★

    Good

  • Sykes rating

A lovely one-bedroom holiday home perched on the outskirts of Weymouth, Dorset. Romantic. Near a beach. Pet-free. Close to amenities. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1114655)

  • Wi-fi
  • Washing machine

  • 10% off - Wed 4th Mar to 30th Apr 2026


for 7 nights $738

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A living room with teal sofas a wooden coffee table a television on a corner stand and a dining area with wooden chairs at Louisa Cottage Brewers Quay Harbour
23
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.4★

    Good

  • Sykes rating

Beautiful and spacious cottage over three floors in Weymouth. Next to the Old Harbour and close to town centre. Beach 1 mile. Pub and shop 5 min. Beach 1 mile. Dorchester 8.5 miles. (Ref. 994354)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights $787

Last booked yesterday
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A front view of a house with windows and door at Guinea Cottage Brewers Quay Harbour
30
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2★

    Good

  • Sykes rating

Two bedroom cottage close to Weymouth harbour. Dog friendly. Close to all amenities. (Ref. 994236)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights $595

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