Short Breaks in Weymouth

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Your search returned 284 cottages.

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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
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

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

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

    7 nights from £531

    Secure your holiday with a 30% deposit* Book now
  • A backyard patio with a glass table and chairs purple flowers a wooden bench and a wooden swing at Anchors Away in Weymouth
    34
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A wonderful three-storey holiday cottage settled in the seaside resort of Weymouth in Dorset. (Ref. 1096129)

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

    7 nights from £708

    Secure your holiday with a 30% deposit* Book now
  • An outdoor patio with a round wooden table and six chairs next to a garden and stone wall overlooking the sea at Beach View Apartment 2 in Greenhill
    35
    Greenhill, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Excellent period apartment in Weymouth close to the esplanade. (Ref. 993988)

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

    7 nights from £1065

    Secure your holiday with a 30% deposit* Book now
  • A brick house with a brown door and windows a driveway wooden benches and a garage at Chickerell House Weymouth
    32
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Chickerell House is a pleasant, detached holiday home resting in the seaside town of Weymouth, Dorset. (Ref. 1152691)

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

    7 nights from £736

    Secure your holiday with a 30% deposit* Book now
  • A brick house with a black front door and three windows with gravel and plants in the front garden at The Pines in Weymouth
    Property has offers
    28
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Tucked in a quiet location in Weymouth, The Pines is a modern holiday home for families or couples. (Ref. 994549)

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

    • £268 off - Mon 29th Dec 2025 to 5th Jan 2026

    7 nights from £703

    Secure your holiday with a 30% deposit* Book now
  • 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 £613

    Secure your holiday with a 30% deposit* Book now
  • 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
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages 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 £621

    Secure your holiday with a 30% deposit* Book now
  • A garden with flowers a wooden arch and a raised deck attached to a brick house at Little Retreat in Upwey
    22
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Village pubs and tea rooms. (Ref. 994358)

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

    7 nights from £485

    Secure your holiday with a 30% deposit* Book now
  • A street view of a blue painted building with white framed windows and two white doors in a row of attached houses
    18
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Located on the harbourside, is this two-bedroom contemporary apartment in Weymouth, Dorset. (Ref. 1017563)

    • Ground floor bedroom
    • Dishwasher
    • Washing machine

    7 nights from £832

    Secure your holiday with a 30% deposit* Book now
  • A garden with a shed and patio overlooking a bay with sailboats at Rainbow's End in Cove Castle
    27
    Cove Castle, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    2-minute walk to Sandsfoot beach and the South West Coast path. (Ref. 994582)

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

    7 nights from £708

    Secure your holiday with a 30% deposit*
    Last booked 1 hour ago
    Book now
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