Winter Short Breaks in Dorset

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Your search returned 480 cottages.

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  • The exterior entrance of a red brick building with blue door and blue trim around windows at Seasides in Weymouth
    Property has offers
    55
    Save £60 with code BFDEAL60
    Weymouth, Dorset
    • Sleeps13
    • Bedrooms6
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Lovingly renovated Seasides offers, beach, sea and harbour views, suitable for large family gatherings close to shops and amenities. (Ref. 1056791)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room
    • Sky TV

    • 20% off - Mon 1st Dec to 21st Dec 2025

    3 nights from Mon 1st Dec $2076

    Secure your holiday with a 30% deposit* Book now
  • A small brick and stone building with a slate roof surrounded by trees and bushes in a garden at The Folly at Castlebridge in Mere
    21
    Save £60 with code BFDEAL60
    Mere, Wiltshire
    • Sleeps2
    • Bedrooms1
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    Enchanting and unusual folly in an idyllic private setting. (Ref. 988942)

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

    3 nights from Mon 8th Dec $710

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with a white door and windows a wooden gate and gravel driveway at Little Brook in Nottington near Weymouth
    26
    Save £60 with code BFDEAL60
    Nottington near Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A quaint stone-built cottage resting on the outskirts of Weymouth. (Ref. 1061544)

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

    3 nights from Mon 8th Dec $732

    Secure your holiday with a 30% deposit* Book now
  • A two-story brick house with a white entrance porch and cobblestone driveway at The Chocolate Box in Weymouth
    37
    Save £60 with code BFDEAL60
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A lovely three-storey house resting in Weymouth, Dorset. (Ref. 1092302)

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

    3 nights from Mon 1st Dec $923

    Secure your holiday with a 30% deposit* Book now
  • A stone house with a light blue door and white framed windows by a small river with ducks and overhanging trees at Duck Cottage in Sutton Poyntz
    44
    Save £60 with code BFDEAL60
    Sutton Poyntz, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. (Ref. 1008404)

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

    3 nights from Tue 6th Jan $707

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of a stone house with multiple wooden windows and a wooden door next to outdoor dining furniture at The Granary Burton Bradstock
    33
    Save £60 with code BFDEAL60
    Burton Bradstock, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A beautifully presented property resting in the pretty village of Burton Bradstock. (Ref. 1069147)

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

    3 nights from Sun 30th Nov $1391

    Secure your holiday with a 30% deposit* Book now
  • A thatched roof cottage next to a white building with parking spaces near trees at Thimble Cottage in Winterborne Stickland near Blandford Forum
    24
    Save £60 with code BFDEAL60
    Winterborne Stickland near Blandford Forum, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    This charming, one-bedroom holiday home rests in Winterborne Stickland near Blandford Forum, Dorset. (Ref. 1068261)

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

    3 nights from Sun 30th Nov $694

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A small dining area with a round table set for four near a window with a view of the beach and ocean at 5 The Beaches Weymouth
    18
    Save £60 with code BFDEAL60
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    Beautiful seafront apartment within the popular resort of Weymouth in Dorset. (Ref. 1003083)

    • Wi-fi
    • Dishwasher

    3 nights from Tue 2nd Dec $653

    Secure your holiday with a 30% deposit*
    Last booked 5 hours ago
    Book now
  • A brick exterior of a cottage with white doors and windows at Rupert Cottage Brewers Quay harbour
    27
    Save £60 with code BFDEAL60
    Brewers Quay harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Sleeping 4 cosy cottage in Weymouth. (Ref. 994605)

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

    3 nights from Tue 3rd Mar $800

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of a building with black doors and windows a wooden picnic table and umbrella on a patio at Rowdens Barn in Winterborne Stickland
    27
    Save £60 with code BFDEAL60
    Winterborne Stickland, Dorset
    • 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

    3 nights from Sat 6th Dec $498

    Secure your holiday with a 30% deposit* Book now
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