Weymouth Holiday Cottages

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Your Weymouth, Dorset search returned 270 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 corner seating area with two black armchairs near bay windows and a side table with a lamp at Two @ No36 in Weymouth
31
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 $982

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Two armchairs with striped cushions by bay windows overlooking a beach at Three @ No36 in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

Three @ No36, a delightful, second-floor apartment situated in the town of Weymouth in Dorset, enjoying sea views with the beach on your doorstep. Smart TV. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162204)

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


for 7 nights From $911

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A brick townhouse with multiple windows and green hedges in front at Plain Sailing in Weymouth
25
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.7★

    Outstanding

  • Sykes rating

Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. En-suite master. Lake view. Pet-friendly. Dorchester 7.8 miles; Bridport 18.6 miles. (Ref. 1153879)

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


for 7 nights From $923

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A brick house exterior with white framed windows a door a mailbox and a small outdoor table with a bench at Goliath in Brewers Quay Harbour
24
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

Beautiful 1 bedroom stable conversion in the heart of the harbour area in Weymouth. WIFI, Close to town centre and beach. Parking for one car. (Ref. 1096825)

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


for 7 nights From $700

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A house with a pink door on a street at Shrimp Cottage in Brewers Quay Harbour
Offer
37
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    5.0★

    Perfect

  • Sykes rating

Shrimp Cottage is a tasteful house in Brewers Quay Harbour, Dorset, this pet-friendly abode boasts Smart TVs and is near the beach and other amenities. Dorchester 9 miles; West Lulworth 15.9 miles (Ref. 1173548)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine

  • $213 off - Fri 7th Aug to 14th Aug 2026

  • $213 off - Fri 14th Aug to 21st Aug 2026


for 7 nights From $816

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A small outdoor seating area with chairs and a table surrounded by flowers in front of a brick house with blue shutters at Garibaldi Cottage in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

Garibaldi Cottage is a lovely, coastal home resting in the town of Weymouth in Dorset, enjoying close proximity to a nearby shop, beach, and pub. Dorchester 8.2 miles; Bridport 20.1 miles. (Ref. 1156408)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights From $728

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A front entrance with a blue door and window at 23 The Maltings in Weymouth
27
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

  • Sykes rating

Dolphin Cottage is a lovely cottage nestled into the bustling seaside town of Weymouth, Dorset, close to a shop, pub, local walks, and beaches. Fortuneswell 4.8 miles; Dorchester 8.9 miles; Bridport 19.5 miles. (Ref. 1179916)

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


for 7 nights From $865

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A detached house with a double garage and driveway at Connaught Gardens in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

Large, modern house nestled on the outskirts of Weymouth, 1 mile from the beach and restaurants. Off-road parking. WiFi. Enclosed garden. (Ref. 1001446)

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


for 7 nights From $1039

Last booked 2 days ago
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Front view of a brick terraced house with bay windows and a black front door at Pedaller's Cottage in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

Located in a quiet residential street in Weymouth, Pedaller’s cottage is a delightful home for families. Short walk to town. WiFi. Pub and shop 5 min. Beach 1 mile. Dorchester 8.6 miles. (Ref. 994539)

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


for 7 nights From $1059

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Front view of three terraced houses with plants and bushes in front at Kingfisher Cottage in Weymouth
19
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

A terrace property resting close to the beach and harbour in Weymouth. Allocated parking for two cars. WiFi. Fortuneswell 4.7 miles; Dorchester 8.9 miles. (Ref. 1038344)

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


for 7 nights From $649

Last booked 2 days ago
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A living room with two grey sofas and a wooden boat-shaped shelf with books at Chesil Retreat Weymouth
32
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 $680

Last booked 2 days ago
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A row of terraced houses with white and yellow facades and a sidewalk at Brewers Quay Harbour
28
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.5★

    Outstanding

  • Sykes rating

A delightful cottage situated next to Weymouth harbour in Dorset. Harbour Views. Family-friendly. Dorchester 8.4 miles; West Lulworth 15.5 miles. (Ref. 1061726)

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


for 7 nights From $1097

Last booked yesterday
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A kitchen with white cabinets marble countertops skylights and floral curtains at Upsidedown House Brewers Quay Harbour
25
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

Located in a quiet location in Weymouth, Upsidedown House is a unique and beautiful holiday home. Pub and shop 2 min. Beach 10 min. Dorchester 8.4 miles. (Ref. 994746)

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


for 7 nights From $1273

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Quay Cottage - 994576 - photo 1
28
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

Quay cottage is a period terraced property in Weymouth. Short walk to town centre. Close to Old Harbour. WiFi. Pub and shop 5 min. Beach 10 min. Dorchester 8.5 miles. (Ref. 994576)

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


for 7 nights From $800

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Exterior of a row of white buildings with balconies and doors including a restaurant named ENZO at Bliss On The Bay Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

A stylish apartment resting on Weymouth's beautiful esplanade. Sleeps 4. Opposite beach. Off road parking. WiFi. Dorchester 7.3 miles; Bridport 20.3 miles. (Ref. 1067722)

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


for 7 nights From $828

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A house facade with windows and doors at 8 Park View Grove Weymouth
40
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms3
  • Pet FriendlyYes

    5.0★

    Perfect

  • Sykes rating

Park View is a welcoming house in Weymouth, Dorset, offering three bedrooms, enclosed rear garden, and easy reach of shop, pub, and beach. Dorchester 8.4 miles; Bridport 19 miles; Charmouth 25.5 miles. (Ref. 1198402)

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


for 7 nights From $832

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Front exterior of a house with a black door two potted plants and pink flowers in a garden at 6 The Terrace Brewers Quay Harbour
42
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. Quality finish. Sea and harbour views. Enclosed garden. Raised elevation. Dorchester 8.5 miles; West Lulworth 15.5 miles. (Ref. 1096352)

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


for 7 nights From $1193

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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
39
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


for 7 nights From $868

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A street view of a row of attached brick houses with dormer windows and a sidewalk at Marina Reach in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.5★

    Outstanding

  • Sykes rating

Ground floor apartment in Weymouth, sleeps 4, wifi, allocated parking, close to the beach, shops and marina. Open plan living kitchen diner. (Ref. 1091449)

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


for 7 nights From $715

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A street view of terraced houses with white doors and windows at Angel Cottage in Weymouth
Offer
25
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

A characterful one-bedroom property resting in Weymouth, Dorset. Close to amenities and a beach. Near an AONB. Couples retreat. Dorchester 6.8 miles; Bridport 18.3 miles. (Ref. 1125691)

  • Wi-fi

  • 10% off - Sat 30th May to 5th Sep 2026


for 7 nights From $545

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