May Half-Term Breaks

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Your search returned 443 cottages.

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  • A gravel driveway with potted plants leading to a group of brick and white cottages with trees around at Little Stables Cottage in Spetisbury
    Property has offers
    30
    Spetisbury, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A delightful, converted stable nestled in a quiet location on a working farm in the village of Spetisbury, Dorset. (Ref. 1127126)

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

    3 nights from Fri 29th May was $1055 $824

    Secure your holiday with a 30% deposit* Book now
  • The front exterior of a brick house with several windows a wooden door and a white garage door at Mariners Rest in Weymouth
    15
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Set in a lovely and quiet residential area of Weymouth, the house is a comfortable getaway for a family. (Ref. 994377)

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

    3 nights from Tue 26th May $797

    Secure your holiday with a 30% deposit* Book now
  • A three story house with a beige exterior stone and concrete walls at Osprey House Portland
    27
    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Detached, large and modern house for large group of friends or big family. (Ref. 994499)

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

    3 nights from Sun 31st May $978

    Secure your holiday with a 30% deposit* Book now
  • A narrow street with houses on the right and a brick wall with plants on the left at Firkin Cottage Brewers Quay Harbour
    22
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms4
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Comfortable renovated cottage with rear garden and close to the town centre. (Ref. 994191)

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

    3 nights from Sun 31st May $699

    Secure your holiday with a 30% deposit* Book now
  • A living room with a TV on a stand a coffee table with board games a clock on the wall and large windows showing a sea view at Beach View Apartment 3 in Greenhill
    19
    Greenhill, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Directly on the seafront. (Ref. 993989)

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

    3 nights from Tue 26th May $913

    Secure your holiday with a 30% deposit* Book now
  • A living room with a wooden coffee table two patchwork chairs a fireplace and a window with an ocean view at Beach Retreat in Weymouth
    40
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A sea-front two-bedroom apartment fronting Weymouth bay, Dorset. (Ref. 1100406)

    • Wi-fi
    • Dishwasher

    3 nights from Tue 26th May $849

    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

    3 nights from Sun 31st May $799

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with a white front door and a paved pathway bordered by trimmed hedges at Knapp Cottage in Chickerell
    39
    Chickerell, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A charming, three-bedroom cottage sitting in Chickerell, Dorset. (Ref. 1086432)

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

    3 nights from Sun 24th May $843

    Secure your holiday with a 30% deposit* Book now
  • A two-story brick house with a double garage and driveway adjacent to trees at 1 Charlotte Close in Talbot Village Poole
    38
    Talbot Village, Poole, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A traditional four-bedroom cottage resting in Talbot Village, Dorset. (Ref. 1105314)

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

    3 nights from Sun 31st May $1063

    Secure your holiday with a 30% deposit* Book now
  • A window seat with two mugs and a muffin on a tray overlooking a carousel and seaside at Shore View in Weymouth
    55
    Weymouth, Dorset
    • Sleeps10
    • Bedrooms5
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. (Ref. 1118900)

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

    3 nights from Sun 31st May $1543

    Secure your holiday with a 30% deposit* Book now
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