May Bank Holidays in Dorset

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Your search returned 417 cottages.

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  • A garden with grass a wooden deck with a swing and a patio with chairs and a table at Blue Waters in Weymouth
    Property has offers
    25
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    A delightful, one-bedroom holiday home resting in Weymouth, Dorset. (Ref. 1133982)

    • Wi-fi
    • Dishwasher

    7 nights from Fri 1st May £865

    Book now
  • A view of rooftops with chimneys and a cliff by the sea at Seaview in Swanage
    Property has offers
    58
    Swanage, Dorset
    • Sleeps7
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    This all-ground-floor cottage rests in the charming seaside resort of Swanage on the Jurassic Coast of Dorset. (Ref. 1012027)

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

    7 nights from Fri 1st May was £1202 £1128

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  • A brick house with black doors and windows a bench and potted plants outside at Meadow View Barn in Bere Regis
    Property has offers
    29
    Bere Regis, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Charming, modern barn located in the Dorset village of Bere Regis. (Ref. 1000906)

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

    • 20% off - Fri 3rd Apr to 17th Apr 2026

    7 nights from Fri 8th May £824

    Last booked 1 hour ago
    Book now
  • An outdoor patio area with tables, chairs, and flower beds outside cream walls with blue doors and windows at The Compass in Swanage
    Property has offers
    24
    Swanage, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Lovely apartment nestled in the thriving Dorest town of Swanage. (Ref. 979371)

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

    7 nights from Sat 9th May was £464 £433

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  • A wooden house with brick foundation surrounded by trees and plants at Willow Brook in Okeford Fitzpaine
    Property has offers
    12
    Okeford Fitzpaine, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    A well-presented barn conversion resting on the outskirts of Okeford Fitzpaine, Dorset. (Ref. 1137516)

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

    7 nights from Fri 1st May £960

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  • A living room with two grey sofas and a wooden boat-shaped shelf with books at Chesil Retreat Weymouth
    Property has offers
    32
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A stylish property resting in the resort of Weymouth, Dorset. (Ref. 1100742)

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

    7 nights from Fri 15th May was £714 £673

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  • A two-story corner house with a pink brick exterior and a bay window at Mermaid House in Brewers Quay Harbour
    Property has offers
    41
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This stylish and neat holiday home rests in Brewers Quay Harbour in Weymouth, Dorset. (Ref. 1093760)

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

    7 nights from Sat 16th May was £705 £670

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  • A patio with a hot tub and a small table and chair set opening onto a grassy field at Deer Lodge in Wimborne Minster
    Property has offers
    41
    Wimborne Minster, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    This detached lodge rests on the outskirts of Wimborne Minster, Dorset. (Ref. 1038027)

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

    • 10% off - Fri 27th Mar to 3rd Apr 2026

    7 nights from Fri 29th May £1152

    Last booked today
    Book now
  • An outdoor patio area with a glass table and six chairs under an umbrella next to a modern house at Bramley Cottage Henley near Langport
    41
    Henley near Langport, Somerset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    An exceptional detached property resting on the outskirts of Langport, Somerset. (Ref. 1074556)

    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Sky TV

    7 nights from Mon 4th May £912

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  • A single-story dark wooden house with multiple windows and a front door on a lawn at Rectory Farm View in Queen Camel near Yeovil
    47
    Queen Camel near Yeovil, Somerset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Bright, spacious ground floor holiday home on the outskirts of Queen Camel, amongst beautiful Somerset countryside. (Ref. 957130)

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

    7 nights from Fri 29th May £819

    Last booked 2 days ago
    Book now
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