May Half-Term Breaks

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    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • A small A-frame house with a wooden deck and stairs surrounded by trees and grass at Apple Tree Lodge in Gillingham
    23
    Gillingham, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Unique, A-frame lodge placed near Gillingham in Dorset. (Ref. 970181)

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

    3 nights from Mon 25th May €484

    Book now
  • A single story house with a tiled roof a chimney and an antenna on a lawn at Broadstones in Bridport
    Property has offers
    37
    Bridport, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A pleasant, detached bungalow resting in Bettiscombe outside Bridport, Dorset. (Ref. 1105472)

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

    • 5% off - Mon 11th May to 6th Jun 2026

    3 nights from Fri 22nd May €619

    Book now
  • Harbour Reach 7 - 1194446 - photo 1
    Property has offers
    26
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Harbour Reach 7, an agreeable second-floor apartment in the town of Weymouth, in Dorset, boasts proximity to the beach, shop and pub and West Dorset Heritage Coast. (Ref. 1194446)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 5% off - Tue 5th May to 27th Jun 2026

    3 nights from Mon 25th May €644

    Last booked yesterday
    Book now
  • A front view of a house with windows and door at Guinea Cottage Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    Two bedroom cottage close to Weymouth harbour. (Ref. 994236)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Fri 22nd May €455

    Book now
  • The front entrance of a house with a green door and a window beside it with plants in black pots on a paved area at Sea Gem in Castletown Portland
    43
    Castletown, Portland, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A spacious, three-storey house settled in Castletown, Portland, Dorset. (Ref. 1107230)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher

    3 nights from Tue 26th May €1100

    Book now
  • A brick terraced house with a green front door and front lawn at The Lookout -The House With A View in Weymouth
    29
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    A well-presented, mid-terrace property resting within the village of Wyke Regis. (Ref. 1006910)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Wed 27th May €785

    Book now
  • An outdoor patio area with a table umbrella and chairs in front of a building with brown doors and windows at Little Barn in Cucklington near Wincanton
    15
    Cucklington near Wincanton, Somerset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Rural semi-detached dairy conversion. (Ref. 1021741)

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

    3 nights from Fri 22nd May €474

    Book now
  • An outdoor tent with a wooden deck table and chairs surrounded by grass and trees at Oak Stockland near Dalwood
    Property has offers
    25
    Stockland near Dalwood, Devon
    • Sleeps6
    • Bedrooms1
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    Oak is a splendid safari tent resting in peaceful Stockland near Dalwood, Devon. (Ref. 1147767)

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

    • 5% off - Thu 9th Apr to 31st May 2026

    3 nights from Fri 29th May €416

    Book now
  • A house with white facade and windows at NO 10 Fortuneswell
    New property
    34
    Fortuneswell, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

    • Dream Cottages rating

    NO 10 is a fine, dog-friendly house situated in Fortuneswell, Dorset, featuring an electric fire, an enclosed courtyard, and easy access to the beach. (Ref. 1200066)

    • Wi-fi
    • Dishwasher

    3 nights from Sat 23rd May €708

    Book now
  • A brick cottage with a paved driveway a wooden door and a small lawn at Frome Lodge House in Frome Whitfield
    Property has offers
    22
    Frome Whitfield, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    A charming, two-bedroom holiday home resting in Frome Whitfield, Dorset. (Ref. 1132783)

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

    3 nights from Sat 23rd May was €686 €554

    Book now
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