Winter Short Breaks in Dorset

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Your search returned 487 cottages.

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  • A white brick exterior of two adjacent houses with black and green doors and windows at Wey Cottage in Weymouth
    17
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.3★

      Good

    • Dream Cottages rating

    Traditional terraced cottage, 3 minutes' walk to the harbour, shop and café. (Ref. 998260)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 29th Nov $599

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  • A row of attached houses with brick and beige facades on a street with sidewalks at Globe Cottage in Weymouth
    27
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Three bedroom terraced property in central Weymouth. (Ref. 1095056)

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

    3 nights from Wed 6th Jan $1028

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  • A brick terraced house with a black front door two windows with shutters and a street lamp in front at Harbour Catch Cottage in Weymouth
    18
    Weymouth, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Traditional cute cottage, in the town centre side of Weymouth harbour. (Ref. 994240)

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

    3 nights from Sun 29th Nov $678

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  • The front exterior of a red brick house with white framed windows and a white front door at 74 Reap Lane Southwell near Weston
    30
    Southwell near Weston, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    74 Reap Lane is a lovely home resting near the village of Weston, on the Isle of Portland in Dorset. (Ref. 1158199)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov $617

    Last booked 7 hours ago
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  • A gravel driveway with potted plants leading to a group of brick and white cottages with trees around at Little Stables Cottage in Spetisbury
    Property has offers
    30
    Spetisbury, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A delightful, converted stable nestled in a quiet location on a working farm in the village of Spetisbury, Dorset. (Ref. 1127126)

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

    3 nights from Fri 4th Dec $790

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  • A living room with teal sofas a wooden coffee table a television on a corner stand and a dining area with wooden chairs at Louisa Cottage Brewers Quay Harbour
    23
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Beautiful and spacious cottage over three floors in Weymouth. (Ref. 994354)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 29th Nov $678

    Last booked 2 days ago
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  • A brick exterior with white doors windows hanging plants and a sculpture at Barley Mews Brewers Quay Harbour
    50
    Brewers Quay Harbour, Dorset
    • Sleeps9
    • Bedrooms4
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    A beautiful conversion of the Devenish Brewery malthouse, just moments from the harbourside. (Ref. 993976)

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

    3 nights from Sun 29th Nov $1612

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  • Exterior view of a white house with flower pots near the door and a tree in the foreground at The Little Cottage in Weymouth
    27
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A quaint, white-washed cottage resting in Weymouth, Dorset. (Ref. 1113457)

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

    3 nights from Sat 28th Nov $747

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  • A living room with two black sofas a television and a glass door leading to an outdoor patio at 23 Millhams Street Christchurch
    26
    Christchurch, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    23 Millhams Street, a stunning renovated Victorian cottage resting in the town of Christchurch in Dorset, close to a shop, a pub, and a beach. (Ref. 1162980)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov $736

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  • An exterior view of a multi-story residential building with balconies and large windows at Townbridge Apartment in Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. (Ref. 1111030)

    • Wi-fi
    • Dishwasher

    3 nights from Sun 29th Nov $843

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