Winter Short Breaks in Dorset

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Your search returned 480 cottages.

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  • An outdoor patio with a hot tub wood siding on the house a table with chairs and an umbrella at Stag Cottage in Lytchett Matravers
    Property has offers
    53
    Save £60 with code BFDEAL60
    • Sleeps6
    • Bedrooms2
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    This stunning, two-bedroom abode is perched in Lytchett Matravers, Dorset. (Ref. 1084628)

    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 10% off - Fri 31st Oct to 18th Dec 2025

    • 5% off - Fri 19th Dec to 31st Dec 2025

    3 nights from Mon 1st Dec $937

    Secure your holiday with a 30% deposit* Book now
  • A modern two story house with parking spaces and cars in front at Mary Bowes Terrace in Southbourne
    30
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    A delightful, ground-floor apartment set in the seaside town of Southbourne. (Ref. 1125968)

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

    3 nights from Mon 15th Dec $509

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A wooden cabin with large glass sliding doors and outdoor seating on a grassy area at Heron Lodge Castle Farm in Wedmore
    25
    Save £60 with code BFDEAL60
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    Luxurious wooden lodge in the village of Wedmore in Somerset. (Ref. 982512)

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

    3 nights from Mon 1st Dec $876

    Secure your holiday with a 30% deposit* Book now
  • A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
    33
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. (Ref. 1133998)

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

    3 nights from Tue 2nd Dec $670

    Secure your holiday with a 30% deposit*
    Last booked 3 hours ago
    Book now
  • A small blue house with patio furniture and potted plants on a tiled patio at Outlook Lodge in Bowleaze
    Property has offers
    28
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    A lodge sleeping four people, Bowleaze area of Weymouth. (Ref. 994500)

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

    3 nights from Sat 6th Dec $881

    Secure your holiday with a 30% deposit* Book now
  • A house with a deck and outdoor furniture at Mallows Byre in Yetminster
    53
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    Mallows Byre is a delightful barn conversion situated in the historic village of Yetminster in Dorset with an outstanding freestanding bath and Smart TV. (Ref. 955342)

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

    3 nights from Mon 15th Dec $610

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with two windows a door and potted plants on a gravel yard with stone steps and greenery at Mill Cottage in Upwey
    30
    Save £60 with code BFDEAL60
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    A charming reverse-level cottage in the village of Upwey, Dorset. (Ref. 1072756)

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

    3 nights from Sun 30th Nov $695

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A white house with a glass porch and wooden railings on a paved patio at Village View in Burton Bradstock
    17
    Save £60 with code BFDEAL60
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    A brightly decorated property resting within the village of Burton Bradstock. (Ref. 1008498)

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

    3 nights from Tue 9th Dec $646

    Secure your holiday with a 30% deposit* Book now
  • Stone cottage exterior with multiple windows a dark wooden door potted plants and a small tree at Tick Tock Cottage in Marnhull
    Property has offers
    30
    Save £60 with code BFDEAL60
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    This fabulous Grade II listed cottage rests in the Dorset village of Marnhull. (Ref. 970616)

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

    3 nights from Fri 5th Dec $530

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A garden with a tree a flower bed and a wooden picnic table outside a two story house at Molly's Place in Boscombe
    Property has offers
    34
    Save £60 with code BFDEAL60
    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    A lovely ground-floor maisonette apartment resting in Boscombe, Dorset. (Ref. 1086302)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • $89 off - Sat 6th Dec to 13th Dec 2025

    3 nights from Thu 11th Dec $589

    Secure your holiday with a 30% deposit* Book now
Most relevant
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Rating (lowest first)
  • Rating (highest first)
  • Location (A to Z)
  • Location (Z to A)
  • Property name (A to Z)
  • Property name (Z to A)
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