Short Breaks in Weymouth

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  • A row of attached houses with one blue house covered in climbing plants and flowers in front at Fenders Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Delightful terraced cottage. (Ref. 998253)

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

    7 nights from From €700

    Book now
  • A two-story brick house behind a stone and brick wall with a black gate and a tree nearby at The Nook in Weymouth
    38
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    The Nook is a charming, pet-friendly cottage resting near the beach in the town of Weymouth in Dorset, boasting a woodburning stove and enclosed garden. (Ref. 1107935)

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

    7 nights from From €662

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  • A stone house with a light blue door and white framed windows by a small river with ducks and overhanging trees at Duck Cottage in Sutton Poyntz
    44
    Sutton Poyntz, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. (Ref. 1008404)

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

    7 nights from From €638

    Book now
  • A balcony with wicker chairs a table and glass panels overlooking a harbor at Bears Apartment in Castletown Portland
    27
    Castletown, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A well-positioned, fourth-floor apartment resting in Castletown, Dorset. (Ref. 1119638)

    • Wi-fi
    • Swimming pool
    • Dishwasher
    • Washing machine

    7 nights from From €645

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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
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A lovely one-bedroom holiday home perched on the outskirts of Weymouth, Dorset. (Ref. 1114655)

    • Wi-fi
    • Washing machine

    7 nights from From €618

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  • Front of a white building with black door and window frames flowers in front at Harbour Reach Brewers Quay Harbour
    36
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Stylish fisherman’s cottage just a few minutes’ walk from Old Harbour in Weymouth. (Ref. 1058438)

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

    7 nights from From €691

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  • A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
    18
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This picturesque cottage, situated in the village of Upwey, with parking. (Ref. 994658)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    7 nights from From €567

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  • A house with a garage and plants in front at Millmead House Annex Portesham
    27
    Portesham, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

    • Dream Cottages rating

    Millmead House Annex is a welcoming holiday annex in Portesham, Dorset, featuring open‑plan living, a woodburning stove and an enclosed garden. (Ref. 1201417)

    • Wi-fi
    • Off-road parking

    7 nights from From €448

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  • An outdoor dining area with a table and six chairs set in front of a bunker entrance with grass on the roof at The Transmitter Bunker in Ringstead
    33
    Ringstead, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    This quirky, converted bunker rests in Ringstead near Preston, Dorset. (Ref. 1131689)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher

    7 nights from From €936

    Book now
  • A living room with a staircase and a sofa at Harbourside in Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Harbourside is a charming, dog-friendly, Grade II listed house in Weymouth, Dorset, set over three stories, with open-plan living and a private courtyard. (Ref. 1172365)

    • Pets go free
    • Wi-fi
    • Washing machine

    7 nights from From €477

    Book now
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