Winter Short Breaks in Dorset

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Your search returned 473 cottages.

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  • Stone terraced houses with white framed windows and a red door on a street at Bowman's Cottage Wakeham Portland
    32
    Wakeham, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A beautiful stone cottage, complete with garden on the quieter end of Portland, however situated on the main bus route to Weymouth and beyond. (Ref. 994021)

    • Wi-fi
    • Washing machine

    3 nights from Fri 28th Nov $678

    Secure your holiday with a 30% deposit* Book now
  • A two-story brick house behind a stone and brick wall with a black gate and a tree nearby at The Nook in Weymouth
    New property
    40
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

    • Dream Cottages rating

    The Nook is a charming, pet-friendly cottage resting near the beach in the town of Weymouth in Dorset, boasting a woodburning stove and enclosed garden. (Ref. 1107935)

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

    3 nights from Sat 29th Nov $673

    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
    Mere, Wiltshire
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • 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 Sat 29th Nov $692

    Secure your holiday with a 30% deposit* Book now
  • A stone and brick house with arched windows a green door a bench and gravel driveway at The Coach House at Lackington Farm in Piddletrenthide
    57
    Piddletrenthide, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Gold Gems Award Winner for Best on the South Coast 2023. (Ref. 1087048)

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

    3 nights from Fri 28th Nov $843

    Secure your holiday with a 30% deposit* Book now
  • A living room with two sofas a small white table with wine glasses and bottle a tv and glass doors to a garden at Pebbles in Burton Bradstock
    19
    Burton Bradstock, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Stylishly renovated bungalow in Burton Bradstock. (Ref. 994537)

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

    3 nights from Sat 29th Nov $958

    Secure your holiday with a 30% deposit* Book now
  • Front view of a two-storey house with white framed windows and doors with flowering bushes in front at Chine Heights in Bournemouth
    32
    Bournemouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A duplex apartment resting in the coastal town of Bournemouth, Dorset. (Ref. 1133748)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 29th Nov $850

    Secure your holiday with a 30% deposit* Book now
  • The facade of a three-story building with bay windows and a sign reading Bay Tree House in Seaton Devon
    61
    Seaton, Devon, Devon
    • Sleeps16
    • Bedrooms8
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A beautiful four-storey townhouse resting in the seaside town of Seaton, Devon. (Ref. 1063005)

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

    3 nights from Sun 30th Nov $2098

    Secure your holiday with a 30% deposit* Book now
  • A wooden lodge with a deck and ramp on a grassy area at Manor Farm Lodge in Bowerchalke
    30
    Bowerchalke, Wiltshire
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    This charming, two-bedroom holiday lodge rests in Bowerchalke, near Broad Chalke, Wiltshire. (Ref. 1111761)

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

    3 nights from Mon 1st Dec $734

    Secure your holiday with a 30% deposit* Book now
  • A row of terraced houses with flowers and bushes in front and a view of the sea at Langham Cottage in Portland
    35
    Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. (Ref. 994321)

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

    3 nights from Fri 28th Nov $539

    Secure your holiday with a 30% deposit* Book now
  • Three modern two story houses with green window frames and stone wall facades with a paved driveway and some plants at Pebbles Reach in Fortuneswell
    42
    Fortuneswell, Dorset
    • Sleeps7
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    An attractive, terraced, three-storey house near Chesil Beach in Fortuneswell, Dorset. (Ref. 1091335)

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

    3 nights from Sun 30th Nov $860

    Secure your holiday with a 30% deposit* Book now
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