Self-Catering Weymouth Cottages

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  • A stone house with a tiled roof and a paved driveway at Sunningdale Rise in Preston
    Property has offers
    43
    Preston, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Sunningdale Rise is a striking, detached home on a gated development with off-road parking, close to a beach, in the village of Preston in Dorset. (Ref. 1149947)

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

    • 10% off - Fri 17th Jul to 2nd Oct 2026

    7 nights from From $1816

    Book now
  • A row of terraced houses with stairs leading to the front doors and balconies above on a clear day at Wessex View in Weymouth
    22
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.3★

      Good

    • Dream Cottages rating

    This is a beautiful ground-floor apartment within a townhouse on the Weymouth seafront in Dorset. (Ref. 1034440)

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

    7 nights from From $694

    Book now
  • A living room with a sofa, coffee table, and dining area at Beachcomb in Weymouth
    28
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

    • Dream Cottages rating

    Beachcomb is a fine third-floor apartment located close to a beach in the town of Weymouth in Dorset, well-positioned to nearby attractions and amenities. (Ref. 1083686)

    • Wi-fi
    • Washing machine

    7 nights from From $763

    Book now
  • The front entrance of a house with a green door and a window beside it with plants in black pots on a paved area at Sea Gem in Castletown Portland
    43
    Castletown, Portland, Dorset
    • Sleeps7
    • Bedrooms4
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A spacious, three-storey house settled in Castletown, Portland, Dorset. (Ref. 1107230)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher

    7 nights from From $1210

    Book now
  • A living room with a blue sofa and ottoman near a fireplace and television at Owls Rest in Weymouth
    36
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A homely, mid-terrace cottage based in Weymouth. (Ref. 1094925)

    • Pets go free
    • Wi-fi
    • Baby-friendly

    7 nights from From $633

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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 $809

    Last booked yesterday
    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 $735

    Last booked yesterday
    Book now
  • A street view showing the entrance door of Little Gull Cottage with steps and potted plants in Weymouth
    21
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Little Gull Cottage is a lovely, three-storey holiday home close to Weymouth’s harbour in Dorset. (Ref. 1144645)

    • Pets go free
    • Wi-fi
    • Baby-friendly

    7 nights from From $719

    Book now
  • A balcony with a round table holding a bottle and two wine glasses with two chairs and a sea view at Sunbeach in Weymouth
    24
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A neat, first-floor apartment set overlooking the Pavillion on Weymouth seafront. (Ref. 1123724)

    • Wi-fi

    7 nights from From $726

    Book now
  • An outdoor hot tub next to a blue house with glass doors and a garden with grass and bushes at Fisherman's Cottage in Southwell
    25
    Southwell, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

    • Dream Cottages rating

    A historic, 18th-century cottage resting in Portland, Dorset. (Ref. 1122551)

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

    7 nights from From $1004

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