May Bank Holidays in Dorset

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Your search returned 414 cottages.

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  • Stone cottages with gravel courtyard and greenery at Coombe Orchard in Swanage
    Property has offers
    17
    Swanage, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Perfect cottage for 2, close to Swanage, Open plan living area for two people, dog friendly. (Ref. 994113)

    • Off-road parking
    • Ground floor bedroom
    • Baby-friendly

    7 nights from Sat 30th May £609

    Book now
  • A driveway with a silver van parked next to a house with a garage and trees at Redcliff View Lodge in Weymouth
    Property has offers
    24
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.1★

      Good

    • Dream Cottages rating

    Sleeps six in Weymouth, patio garden. (Ref. 994586)

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

    7 nights from Sat 2nd May £660

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  • A single story wooden house with gray roof a blue bench outside at Beside the Sea in Eype
    Property has offers
    24
    Eype, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A charming two-bedroom chalet resting on Eypes Mouth Chalet Park in Eype, Dorset. (Ref. 1089040)

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

    7 nights from Sat 2nd May £643

    Last booked 8 hours ago
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  • A house with stone and wooden exterior at Everdene Upwey near Weymouth
    Property has offers
    46
    Upwey near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. (Ref. 932160)

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

    7 nights from Fri 29th May £1133

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  • A stone cottage with white doors and windows along a narrow road with plants and flowers growing at the base of the wall at Pippins Loders in Bridport
    Property has offers
    29
    Bridport, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Stone three bedroom cottage near Bridport. (Ref. 994548)

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

    7 nights from Sat 9th May was £781 £776

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  • A brick exterior with white doors windows hanging plants and a sculpture at Barley Mews Brewers Quay Harbour
    Property has offers
    50
    Brewers Quay Harbour, Dorset
    • Sleeps9
    • Bedrooms4
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    A beautiful conversion of the Devenish Brewery malthouse, just moments from the harbourside. (Ref. 993976)

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

    7 nights from Sat 30th May was £1366 £1210

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  • 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

      4.6★

      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

    7 nights from Fri 1st May £654

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  • A brick two-story house with balconies and a hedge in front at Harbour Reach 6 in Weymouth
    24
    Weymouth, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A wonderful apartment that sleeps up to three people resting in Weymouth, Dorset. (Ref. 1057385)

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

    7 nights from Fri 15th May £470

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  • A patio with a metal table and two chairs outside a building with white framed windows and a glass door at 1 Cowdea Farm in Bettiscombe near Beaminster and Bridport
    Property has offers
    31
    Bettiscombe near Beaminster and Bridport, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A ground floor, semi-detached stone barn conversion on edge of Bettiscombe in Dorset. (Ref. 1857)

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

    • 5% off - Fri 6th Mar to 30th Apr 2026

    7 nights from Fri 1st May £720

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  • The front exterior of a red brick house with white framed windows and a white front door at 74 Reap Lane Southwell near Weston
    Property has offers
    30
    Southwell near Weston, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    74 Reap Lane is a lovely home resting near the village of Weston, on the Isle of Portland in Dorset. (Ref. 1158199)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from Fri 1st May was £512 £491

    Last booked yesterday
    Book now
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