Winter Short Breaks in Dorset

Your search returned 499 cottages.

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    How reviews work

    A property's star rating is the average of the star ratings received from guests that wish for their review to be published

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    Beamed, single-storey holiday cottage near Winterborne Stickland. (Ref. 905898)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 5% off - Wed 1st Jul to 31st Aug 2026

    3 nights from Sat 28th Nov $528

    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    The Elbow is a charming house with period features and a garden, within the picturesque Dorset National Landscape in the village of Frampton in Dorset. (Ref. 1151302)

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

    3 nights from Sun 29th Nov $741

    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Dream Cottages rating

    Swanny View is a welcoming caravan featuring open‑plan living, enclosed decking with furniture, EV charging on‑site and easy access to local amenities. (Ref. 1201196)

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

    3 nights from Sun 29th Nov $547

    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    A charming chalet-style bungalow resting within the town of West Bay. (Ref. 1013337)

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

    3 nights from Sat 28th Nov $994

    • Sleeps33
    • Bedrooms14
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    This stunning historic manor nestles in the heart of Milton on Stour, Dorset. (Ref. 1026929)

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

    3 nights from Sat 28th Nov $6723

    • Sleeps12
    • Bedrooms6
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    Woodlands House is an impressive, dog-friendly retreat near the beach in Ringwood, Dorset, offering a hot tub, ground-floor living, and a balcony. (Ref. 1194318)

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

    3 nights from Sat 28th Nov $2149

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Half Pint Cottage, a lovely, 250-year-old dwelling situated in the town of Beaminster in Dorset, with a pet-friendly policy and a short walk from a pub. (Ref. 1153238)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Sat 28th Nov $581

    Last booked 1 hour ago
    Book now
    • 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

    3 nights from Sun 29th Nov $704

    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.3

      Good

    • Dream Cottages rating

    This is a beautiful ground-floor apartment within a townhouse on the Weymouth seafront in Dorset. (Ref. 1034440)

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

    3 nights from Sun 29th Nov $653

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    Delightful terraced cottage. (Ref. 998253)

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

    3 nights from Sun 29th Nov $803

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