Winter Short Breaks in Dorset

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Your search returned 472 cottages.

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  • 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 €736

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A backyard view of a brick two-story house with patio furniture and a pond in front at Agua de Plata 16 Wakeling Island Silverlake in Dorchester
    33
    Dorchester, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. (Ref. 1138508)

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

    3 nights from Sat 29th Nov €887

    Secure your holiday with a 30% deposit* Book now
  • Exterior of a stone cottage with a thatched roof white door and windows with plants around the entrance at Lilac Cottage in Burton Bradstock
    Property has offers
    29
    Burton Bradstock, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Character cottage in the coastal village of Burton Bradstock, sleeping four. (Ref. 994332)

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

    • 10% off - Fri 18th Jul to 26th Jul 2025

    3 nights from Tue 2nd Dec €717

    Secure your holiday with a 30% deposit* Book now
  • A barn style house with gravel driveway and green field at Shepherd's Barn Between Milborne St Andrew and Winterborne Whitechurch
    29
    Between Milborne St Andrew and Winterborne Whitechurch, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A superb, detached barn conversion set in the countryside near Winterborne Whitechurch. (Ref. 5188)

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

    3 nights from Sun 7th Dec €588

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A living room with a TV cabinet, armchair, ottoman, fireplace, and dining table with chairs at Quarrier's Rest in Swanage
    32
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    This charming, two-bedroom holiday home rests in Swanage, Dorset. (Ref. 1124578)

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

    3 nights from Sat 29th Nov €600

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A garden with a deck, table, and chairs overlooking the sea at Hoppapill House in Bournemouth
    48
    Bournemouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A fantastic ground-floor apartment located in West Cliff near Bournemouth, Dorset. (Ref. 1083610)

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

    3 nights from Sat 29th Nov €1558

    Secure your holiday with a 30% deposit* Book now
  • An exterior view of a building with a door and windows and flower pots at the entrance at Sandy Haven in Swanage
    35
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Sandy Haven is a delightful, ground-floor apartment resting in Swanage, Dorset. (Ref. 1140492)

    • Wi-fi
    • Ground floor bedroom

    3 nights from Sun 1st Mar €593

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A balcony with two chairs a table with a bottle of champagne and glasses overlooking greenery and water at Waters Edge in Wyke Regis
    35
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Modern family house located on the edge of Weymouth, with sea views. (Ref. 994759)

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

    3 nights from Fri 28th Nov €733

    Secure your holiday with a 30% deposit*
    Last booked 4 hours ago
    Book now
  • A backyard with a green lawn a patio dining set with an umbrella and a house with large windows and a sloped roof at Kings Cottage - South in Broad Chalke
    52
    Broad Chalke, Wiltshire
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Exceptional, lovingly restored cottage in Wiltshire's beautiful Chalke Valley. (Ref. 988982)

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

    3 nights from Fri 28th Nov €1180

    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 €848

    Secure your holiday with a 30% deposit* Book now
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