Dorset Holiday Cottages for 2026

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  • A row of terraced houses with white and yellow facades and a sidewalk at Brewers Quay Harbour
    Property has offers
    28
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A delightful cottage situated next to Weymouth harbour in Dorset. (Ref. 1061726)

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

    • 10% off - Sat 16th May to 13th Jun 2026

    7 nights from $1121

    Book now
  • An outdoor area with a table and umbrella at Corner Barn in Winterborne Stickland
    Property has offers
    42
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Superb single-storey barn conversion near Winterborne Stickland in an Area Of Outstanding Natural Beauty. (Ref. 19285)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    • 10% off - Tue 5th May to 30th Jun 2026

    7 nights from $635

    Last booked yesterday
    Book now
  • A glass table with sunglasses fruit bowl champagne bottle and glasses overlooking a beach and sea at 123 On The Sea in Weymouth
    30
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    123 On The Sea is a lovely, two-bedroom apartment residing in Weymouth, Dorset. (Ref. 1133961)

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

    7 nights from $724

    Last booked yesterday
    Book now
  • A stone building facade with multiple windows flower boxes and a wrought iron fence at The Esplanade in Weymouth
    85
    Weymouth, Dorset
    • Sleeps18
    • Bedrooms9
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    The Esplanade is a stunning, nine-bedroom holiday dwelling residing in Weymouth, Dorset. (Ref. 1123341)

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

    7 nights from $3552

    Book now
  • A balcony with two chairs a table with a bottle of champagne and glasses overlooking greenery and water at Waters Edge in Wyke Regis
    35
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Modern family house located on the edge of Weymouth, with sea views. (Ref. 994759)

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

    7 nights from $904

    Last booked yesterday
    Book now
  • Quay Cottage - 994576 - photo 1
    28
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Quay cottage is a period terraced property in Weymouth. (Ref. 994576)

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

    7 nights from $817

    Book now
  • A living room with black leather sofas a glass coffee table with flowers and a lamp by the window at Harbourside Haven Apartment 3 in Weymouth
    17
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    An immaculate second-floor apartment resting in the centre of Weymouth. (Ref. 1059264)

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

    7 nights from $932

    Book now
  • A dining and living area with a round table set for four near large windows and a glass door overlooking an outdoor area with a lighthouse visible beyond at Coastguard View in Portland Bill
    27
    Portland Bill, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Coastguard View is a lovely holiday cottage resting near the coast in Portland Bill on the Isle of Portland, Dorset with a Smart TV and open-plan space. (Ref. 1169819)

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

    7 nights from $803

    Book now
  • A stone farmhouse with blue doors and windows beside a gravel driveway and lawn at Stapleford Farm Hooke near Beaminster
    141
    Hooke near Beaminster, Dorset
    • Sleeps20
    • Bedrooms10
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    Stapleford Farm is a wonderful farm stay located in the charming little village of Hooke near Beaminster, Dorset and has several en-suite bedrooms. (Ref. 1172799)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Washing machine
    • Games room

    7 nights from $3720

    Book now
  • A brick house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
    24
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Situated in a gated complex near Weymouth harbour. (Ref. 994560)

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

    7 nights from $1063

    Book now
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