Winter Short Breaks in Dorset

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Your search returned 487 cottages.

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    • Sleeps10
    • Bedrooms5
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. (Ref. 1118900)

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

    3 nights from Sat 28th Nov £1157

    • 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 30th Nov £417

    Last booked yesterday
    Book now
    • 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 Mon 30th Nov £358

    • 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 Sun 29th Nov £477

    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    Harbour Retreat is an eclectic first-floor apartment close to the harbour and beach, with roadside parking, in the heart of Weymouth in Dorset. (Ref. 1164179)

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

    3 nights from Sat 28th Nov £435

    Last booked 2 days ago
    Book now
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    A well-presented property nestled in the heart of Weymouth, Dorset. (Ref. 1134491)

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

    3 nights from Sat 28th Nov £563

    • Sleeps6
    • Bedrooms4
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    Amy Cottage is a beautiful thatched cottage with a toasty gas fire and accepting pets, located in Dorset's West Lulworth on the Jurassic coastline. (Ref. 1166887)

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

    3 nights from Sat 28th Nov £731

    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4

      Good

    • Dream Cottages rating

    Detached property in village of Sutton Poyntz. (Ref. 994127)

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

    3 nights from Sat 28th Nov £823

    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    Pendennis, a charming listed cottage in the heart of the beautiful town of Sherborne, Dorset. (Ref. 1148488)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Dishwasher
    • Washing machine

    3 nights from Sun 29th Nov £406

    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    This sweet semi-detached dairy conversion rests in the village of Cucklington in Somerset. (Ref. 1021740)

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

    3 nights from Sat 28th Nov £476

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