May Half-Term Breaks

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Your search returned 342 cottages.

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  • The front of a stone building with two doors and multiple windows and a small patio with a chair
    28
    Swanage, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Honeypot Cottage is a conventional, three-storey cottage situated near Swanage Beach in Swanage, Dorset, boasting a Smart TV and enclosed courtyard. (Ref. 1164485)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 31st May €639

    Last booked yesterday
    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

    3 nights from Sun 31st May €647

    Last booked 2 days ago
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  • A coastal area with a golf course a road and a residential neighborhood at Bayview Cottage in Southbourne
    24
    Southbourne, Dorset
    • Sleeps8
    • Bedrooms3
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    A well-positioned, three-bedroom cottage resting in Southbourne, Dorset. (Ref. 1165067)

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

    3 nights from Sun 31st May €799

    Last booked 5 hours ago
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  • A living room with a blue armchair a colorful armchair a television a small fireplace and blue curtains at The Skipper's House in Weymouth
    36
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A delightful, three bed property nestled in the heart of Weymouth, Dorset. (Ref. 1132346)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 24th May €640

    Last booked 2 days ago
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  • Sunny Croft - 977681 - photo 1
    28
    Broadmayne near Dorchester, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Sunny Croft is a delightful 1930s bungalow in Broadmayne, near Dorchester, Dorset. (Ref. 977681)

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

    3 nights from Sun 31st May €844

    Book now
  • A brick house with white framed windows a white garage door and a paved driveway at Portside Greenhill Weymouth
    24
    Greenhill Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    This plush, two-storey property is located in the Greenhill suburb of Weymouth, Dorset. (Ref. 1093991)

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

    3 nights from Fri 29th May €632

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  • A front view of a house with windows and door at Guinea Cottage Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    Two bedroom cottage close to Weymouth harbour. (Ref. 994236)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 31st May €452

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  • Terraced houses with bay windows and colored doors on a street at 26 High West in Weymouth
    27
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    26 High West is a beautifully-presented townhouse located near the harbour in the lovely town of Weymouth, Dorset. (Ref. 1135362)

    • Wi-fi
    • Dishwasher

    3 nights from Mon 1st Jun €457

    Book now
  • A stone and wood house with a tiled roof and grass in front at The Courthouse in Sutton Poyntz
    20
    Sutton Poyntz, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Detached property in village of Sutton Poyntz. (Ref. 994127)

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

    3 nights from Mon 1st Jun €937

    Last booked yesterday
    Book now
  • A living room with two blue sofas and a wooden coffee table next to a fireplace and dining area in the background at Day Cottage in Weymouth
    40
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.3★

      Good

    • Dream Cottages rating

    A delightful, terraced cottage nestled into the coastal town of Weymouth, Dorset. (Ref. 1124105)

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

    3 nights from Mon 1st Jun €454

    Book now
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