May Half-Term Breaks

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Your search returned 342 cottages.

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  • A large two-story house with multiple sliding glass doors and windows and outdoor seating on a grassy yard at Shutts House Garden Apartment in Coombe Bissett
    32
    Coombe Bissett, Wiltshire
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Absolutely stunning, luxurious ground floor accommodation at the eastern end of Wiltshire's beautiful Chalke Valley. (Ref. 1016405)

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

    3 nights from Fri 22nd May £1057

    Last booked 2 days ago
    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

      4.7★

      Outstanding

    • Dream Cottages rating

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

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

    3 nights from Wed 27th May £761

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  • Exterior of a single story stone and brick cottage with black windows and doors and two flower pots at Keepers Cottage in Winterborne Stickland
    42
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Charming, characterful, single-storey barn conversion. (Ref. 905895)

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

    3 nights from Tue 26th May £605

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  • A harbor with boats docked and modern buildings in the background at The Boardwalk in West Bay
    19
    West Bay, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Central location of West Bay, 1st floor apartment. (Ref. 994014)

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

    3 nights from Sun 24th May £659

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  • 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 £647

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  • 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

    3 nights from Mon 1st Jun £2610

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  • A blue two-story building with bay windows and white doors on a brick street at Tradewinds Brewers Quay Harbour
    17
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. (Ref. 994737)

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

    3 nights from Tue 26th May £733

    Book now
  • A brick terraced house with a white front door gravel front garden and small plants at Home Waters in Wyke Regis
    23
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Off road parking. (Ref. 994270)

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

    3 nights from Mon 1st Jun £608

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  • A street view of a cottage with brick and stone walls with bushes and flowers outside at Apple Tree Cottage in Shillingstone near Sturminster Newton
    26
    Shillingstone near Sturminster Newton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A cosy brick-and-flint terraced cottage, within the pretty Dorset village of Shillingstone. (Ref. 925256)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 31st May £420

    Book now
  • The driveway and entrance of a house with trees plants a small shed and a black cat at Nuthatch in Honiton
    13
    Honiton, Devon
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A delightful, single-storey home resting in Stockland near Honiton, Devon. (Ref. 1131012)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub

    3 nights from Tue 26th May £492

    Book now
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