Weekend Breaks in Weymouth

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Your Weymouth, Dorset search returned 304 cottages

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  • 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

3 nights from £622

  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • 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

3 nights from £552

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.2

    Good

  • Sykes rating

Located close to the town centre, Sea King house is a modern holiday home sleeping up to 5 people. Welcomes two dogs. Pub and shop 7 min. Beach 1.5 miles. Dorchester 8.7 miles. (Ref. 994638)

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

3 nights from £745

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Weyside is a fantastic apartment in the seaside town of Weymouth, located in Dorset, boasting close proximity to the beach as well as several amenities. Dorchester 8.2 miles; Bridport 18.8 miles. (Ref. 1164944)

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

3 nights from £642

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Royal Terrace Sunset is a contemporary apartment situated along the coast in the heart of Weymouth, Dorset, boasting a short walk to a pub and shop. Dorchester 7.7 miles; Bridport 18.9 miles. (Ref. 1173496)

    3 nights from £463

    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7

      Outstanding

    • Sykes rating

    This picturesque cottage, situated in the village of Upwey, with parking. Short drive to Weymouth. Close to pub and tea rooms. Lovely walks nearby. (Ref. 994658)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from £472

    Last booked yesterday
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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6

      Outstanding

    • Sykes rating

    This beautiful three-bedroom property resides in West Lulworth, Dorset. Off-road parking. In an AONB. En-suite bedrooms. Close to amenities and a beach. Wareham 8.8 miles; Weymouth 15.3 miles. (Ref. 1126738)

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

    3 nights from £760

    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5

      Outstanding

    • Sykes rating

    Superb, modern semi-detached holiday cottage, one of five on-site, on the edge of the Dorset village of Upwey, near Weymouth. Tastefully furnished. En-suite, Smart TVs. Dog-friendly. Short drive to Weymouth beach. Weymouth 3.5 miles. (Ref. 932161)

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

    3 nights from £653

    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8

      Outstanding

    • Sykes rating

    Miller’s Cottage is a snug and romantic dwelling located in the village of Puddletown, nearby a river in Dorset, with a woodburning stove and welcoming one pet. Dorchester 5.5 miles. (Ref. 1160443)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from £359

    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.4

      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

    3 nights from £1114

    Last booked yesterday
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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.3

      Good

    • Sykes rating

    Three bedroomed bungalow located just half a mile from Ringstead Beach. A large garden, welcomes 2 dogs, a good base for walking the coast path. (Ref. 994807)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher
    • Baby-friendly
    • 20% off - Fri 24th Oct to 31st Oct 2025

    • 10% off - Fri 31st Oct to 28th Nov 2025

    3 nights from £501

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5

      Outstanding

    • Sykes rating

    A delightful, mid-terrace cottage resting in Brewers Quay Harbour, Dorset. Designated parking. Pet-friendly. Enclosed garden. Weymouth 0.6 miles; Dorchester 8.8 miles; West Lulworth 15.7 miles. (Ref. 1084006)

    • Dishwasher
    • Washing machine

    3 nights from £578

    Last booked 2 days ago
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    • 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

    3 nights from £656

    • Sleeps6
    • Bedrooms4
    • PetsNo

      4.7

      Outstanding

    • Sykes rating

    Comfortable renovated cottage with rear garden and close to the town centre. Garden with furniture. Pub 5 mins. Beach 1 mile. Dorchester 9 miles. (Ref. 994191)

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

    3 nights from £510

    • Sleeps4
    • Bedrooms2
    • PetsNo
    • 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

    3 nights from £499

    • 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

    3 nights from £641

    • Sleeps15
    • Bedrooms6
    • PetsYes

      4.8

      Outstanding

    • Sykes rating

    Anchor House is a stunning, pet-friendly townhouse with a private hot tub in the heart of Weymouth, Dorset, close to local amenities and the beach. Dorchester 7.8 miles; Bridport 19.9 miles. (Ref. 1105510)

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

    3 nights from £1259

    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0

      Perfect

    • Sykes rating

    Garland is a delightful abode 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. 1105442)

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

    3 nights from £522

    Last booked 8 hours ago
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    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Sykes rating

    Coastguard Lookout is a modern, reverse-level house near a beach in Wyke Regis, Dorset, with off-road parking, Juliet balcony, and underfloor heating. Weymouth 2.5 miles; Dorchester 9.6 miles. (Ref. 1169223)

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

    3 nights from £437

    Last booked yesterday
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    • Sleeps7
    • Bedrooms3
    • PetsNo

      4.6

      Outstanding

    • Sykes rating

    A well-positioned, three-storey home resting in Fortuneswell, Dorset. Sea views. Close to amenities and the beach. Family-friendly. Private decked area. Near AONB. Weymouth 5.3 miles. (Ref. 1120221)

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

    3 nights from £561