Winter Short Breaks in Dorset

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Your search returned 253 cottages.

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  • An outdoor patio area with a glass table and black chairs with flowers and wine glasses at 47 Church Street in Lyme Regis
    Property has offers
    50
    Lyme Regis, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Lyme Bay Holidays rating

    47 Church Street is a beautiful, three-storey and dog-friendly house situated in the seaside town of Lyme Regis, Dorset, boasting an enclosed garden. (Ref. 1164169)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 10% off - Tue 25th Nov to 31st Dec 2025

    3 nights from Sun 21st Dec $823

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A street view of three adjoining houses painted blue white and yellow with windows and doors at Monmouth Cottage in Lyme Regis
    23
    Lyme Regis, Dorset
    • Sleeps6
    • Bedrooms4
    • PetsNo

      4.6★

      Outstanding

    • Lyme Bay Holidays rating

    A character cottage in the centre of Lyme Regis in Dorset. (Ref. 1106299)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 21st Dec $684

    Secure your holiday with a 30% deposit* Book now
  • A sitting room with two sofas a wooden coffee table a TV and a window with curtains at The Old Bakehouse in Lyme Regis
    16
    Lyme Regis, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Lyme Bay Holidays rating

    Well-presented holiday cottage in the heart of Lyme Regis in Dorset. (Ref. 1105757)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Sun 21st Dec $812

    Secure your holiday with a 30% deposit* Book now
  • A balcony with potted plants and an open door leading inside overlooking the sea at Bell Cliff House in Lyme Regis
    37
    Lyme Regis, Dorset
    • Sleeps8
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • Lyme Bay Holidays rating

    An idyllic holiday home lying at the heart of Lyme Regis in Dorset. (Ref. 1111805)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Mon 5th Jan $1495

    Secure your holiday with a 30% deposit* Book now
  • A living room with a brown sofa white cushioned wooden chair wooden furniture and a door at Greystones Flat in Lyme Regis
    14
    Lyme Regis, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.4★

      Good

    • Lyme Bay Holidays rating

    A ground-floor apartment resting in Lyme Regis, Dorset. (Ref. 1105800)

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

    3 nights from Sun 21st Dec $606

    Secure your holiday with a 30% deposit* Book now
  • A living room with a brown sectional sofa and red and beige cushions next to a wooden coffee table and black armchair at 2 Mill Green Court in Lyme Regis
    Property has offers
    16
    Lyme Regis, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.2★

      Good

    • Lyme Bay Holidays rating

    A first-floor apartment resting in Lyme Regis, Dorset. (Ref. 1106372)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 10% off - Mon 24th Nov to 31st Dec 2025

    3 nights from Thu 1st Jan $699

    Secure your holiday with a 30% deposit* Book now
  • A house with steps and a gate at St Helena, Charmouth
    51
    Charmouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • Lyme Bay Holidays rating

    St Helena is a beautifully renovated, pet-friendly, three-bedroom holiday home set in the heart of the charming coastal village of Charmouth, in Dorset. (Ref. 1116298)

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

    3 nights from Sun 21st Dec $739

    Secure your holiday with a 30% deposit* Book now
  • A living room with grey sofas a coffee table a wood stove and large windows at Pippin in Charmouth
    27
    Charmouth, Dorset
    • Sleeps8
    • Bedrooms3
    • PetsNo

      4.0★

      Good

    • Lyme Bay Holidays rating

    An outstanding holiday home close to Charmouth in Dorset. (Ref. 1106546)

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

    3 nights from Tue 23rd Dec $911

    Secure your holiday with a 30% deposit* Book now
  • A living room with wooden floor a white sofa two armchairs and a floor lamp at Lyme Time in Lyme Regis
    17
    Lyme Regis, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.3★

      Good

    • Lyme Bay Holidays rating

    A stylish first-floor apartment in the heart of Lyme Regis in Dorset. (Ref. 1106525)

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

    3 nights from Sun 21st Dec $819

    Secure your holiday with a 30% deposit* Book now
  • A brick terraced house with white window frames and a pathway leading to the front door at 3 Cobb View Lyme Regis
    17
    Lyme Regis, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.3★

      Good

    • Lyme Bay Holidays rating

    A seaside second-floor apartment resting in Lyme Regis, Dorset. (Ref. 1105767)

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

    3 nights from Sun 21st Dec $758

    Secure your holiday with a 30% deposit* Book now
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