May Half-Term Breaks

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Your search returned 342 cottages.

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  • A paved driveway with flower pots alongside a single story house with green doors and stone accents at Bumble Bee Retreat in Tytherleigh
    26
    Tytherleigh, Devon
    • Sleeps4
    • Bedrooms1
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    This charming, single-storey cottage rests in the beautiful countryside of Tytherleigh, Devon. (Ref. 1134052)

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

    3 nights from Mon 1st Jun €725

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  • An outdoor patio with a round wooden table and six chairs next to a garden and stone wall overlooking the sea at Beach View Apartment 2 in Greenhill
    35
    Greenhill, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Excellent period apartment in Weymouth close to the esplanade. (Ref. 993988)

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

    3 nights from Tue 26th May €1226

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  • A brick building with multiple bay windows and doors along a street at The BoBo House in Weymouth
    56
    Weymouth, Dorset
    • Sleeps12
    • Bedrooms6
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    The BoBo House is a delightful terraced holiday home resting in the popular coastal town of Weymouth in Dorset set over four floors and near the beach. (Ref. 1059621)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Games room

    3 nights from Sun 31st May €1057

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  • Stone house with wooden door and four windows and plants in front at Norden House in Maiden Newton
    29
    Maiden Newton, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A character filled property resting in the pretty village of Maiden Netwon in Dorset. (Ref. 1072294)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Sat 30th May €889

    Last booked yesterday
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  • The exterior of a brick house with a tiled roof a black door a paved path and plants at Badbury Lodge Brewers Quay Harbour
    26
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Mon 1st Jun €609

    Last booked yesterday
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  • A row of houses with a white picket fence and small garden in front at Smugglers Cottage in Christchurch
    Property has offers
    32
    Christchurch, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A pretty, one-bedroom cottage resting in Christchurch, Dorset. (Ref. 1098695)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 40% off - Fri 27th Feb to 25th Sep 2026

    3 nights from Sun 24th May was €1058 €735

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  • A living room with a TV cabinet, armchair, ottoman, fireplace, and dining table with chairs at Quarrier's Rest in Swanage
    Property has offers
    32
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    This charming, two-bedroom holiday home rests in Swanage, Dorset. (Ref. 1124578)

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

    3 nights from Fri 22nd May €1059

    Last booked yesterday
    Book now
  • Two triangular wooden cabins with stairs surrounded by trees and grass at Rose Lodge in Milton on Stour
    30
    Milton on Stour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    This cosy lodge on a peaceful15 acre site, is resting near village of Milton on Stour in Dorset. (Ref. 967741)

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

    3 nights from Tue 26th May €618

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  • A living room with a sofa armchair wooden chest coffee table dining table and plants at Beach Side in West Bay
    26
    West Bay, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A delightful, ground-floor apartment resting in West Bay, Dorset. (Ref. 1095399)

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

    3 nights from Mon 1st Jun €533

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  • Exterior view of a brick building with balconies windows and surrounding garden at Ocean Watch 5 in Greenhill
    17
    Greenhill, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Modern, bright apartment with sea views over to Weymouth Bay. (Ref. 1098447)

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

    3 nights from Sun 31st May €791

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