Chesil Beach Holiday Cottages

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  • A row of terraced houses with different colored facades along a street at Old Harbour Townhouse in Weymouth
    31
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Old Harbour Townhouse, a delightful, three-storey abode set in the seaside town of Weymouth in Dorset. (Ref. 1159836)

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

    7 nights from €827

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  • A driveway with a silver van parked next to a house with a garage and trees at Redcliff View Lodge in Weymouth
    24
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.1★

      Good

    • Dream Cottages rating

    Sleeps six in Weymouth, patio garden. (Ref. 994586)

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

    7 nights from €758

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  • Exterior view of three adjacent terraced houses with bay windows and chimneys at Harbourside House in Brewers Quay Harbour
    50
    Brewers Quay Harbour, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    Beautiful holiday cottage over three floors beside Old Harbour in Weymouth. (Ref. 994256)

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

    7 nights from €1570

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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
    68
    Ringstead near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Standby Generator Bunker, an impressive abode, rests in rural Ringstead in Dorset, enjoying sea views, a pet-friendly policy, and a woodburning stove. (Ref. 1137374)

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

    7 nights from €1230

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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
    24
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A stylish apartment resting on Weymouth's beautiful esplanade. (Ref. 1067722)

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

    7 nights from €726

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  • Exterior of a single story cottage with two windows and a wooden door with plants in pots outside at Toll Lodge in Frampton
    23
    Frampton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A wonderful cosy 2-bedroom ground floor annex, welcomes 1 dog, Wifi, Wood burner, Close to Country walks, 4 miles to Dorchester, 9 Miles to Weymouth. (Ref. 994729)

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

    7 nights from €585

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  • A living room with sofas and cushions near glass doors with curtains and a rug at Admirals Retreat in Weymouth
    25
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Perfect couples retreat with WIFI. (Ref. 993912)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from €588

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  • A row of stone cottages with thatched roofs and white framed windows along a sloped street at Bramble Cottage in Burton Bradstock
    29
    Burton Bradstock, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Character cottage in Burton Bradstock, sleeping 5 people. (Ref. 994024)

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

    7 nights from €806

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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
    Property has offers
    38
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages 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. (Ref. 1140944)

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

    • 10% off - Sun 12th Apr to 1st May 2026

    7 nights from €780

    Last booked 4 hours ago
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  • A dining table set with plates glasses and bread next to a living room with sofa armchairs coffee table and glass doors with green curtains at Newton's Cove View in Weymouth
    21
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Upper ground floor apartment in the Admiral’s Quarter development. (Ref. 994438)

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

    7 nights from €663

    Last booked 2 days ago
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