Winter Short Breaks in Dorset

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Your search returned 487 cottages.

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  • A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
    18
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    This picturesque cottage, situated in the village of Upwey, with parking. (Ref. 994658)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sat 28th Nov £485

    Last booked 4 hours ago
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  • A large two-story house with multiple sliding glass doors and windows and outdoor seating on a grassy yard at Shutts House Garden Apartment in Coombe Bissett
    32
    Coombe Bissett, Wiltshire
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Absolutely stunning, luxurious ground floor accommodation at the eastern end of Wiltshire's beautiful Chalke Valley. (Ref. 1016405)

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

    3 nights from Sat 28th Nov £1057

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  • The exterior of a brick house with a tiled roof a black door a paved path and plants at Badbury Lodge Brewers Quay Harbour
    26
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 29th Nov £529

    Last booked 2 days ago
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  • A backyard patio with a glass table and chairs purple flowers a wooden bench and a wooden swing at Anchors Away in Weymouth
    34
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A wonderful three-storey holiday cottage settled in the seaside resort of Weymouth in Dorset. (Ref. 1096129)

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

    3 nights from Sun 29th Nov £708

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  • A dining table set with plates glasses and bread next to a living room with sofa armchairs coffee table and glass doors with green curtains at Newton's Cove View in Weymouth
    21
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Upper ground floor apartment in the Admiral’s Quarter development. (Ref. 994438)

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

    3 nights from Sun 29th Nov £497

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  • A garden with various plants and flowers outside a stone cottage with thatched roof at The Elbow in Frampton
    44
    Frampton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    The Elbow is a charming house with period features and a garden, within the picturesque Dorset National Landscape in the village of Frampton in Dorset. (Ref. 1151302)

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

    3 nights from Sun 29th Nov £562

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  • A brick house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
    24
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in a gated complex near Weymouth harbour. (Ref. 994560)

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

    3 nights from Sun 29th Nov £650

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  • A large stone manor house with bay windows and ivy on the walls with a garden and small pond in front at Milton Manor in Milton On Stour
    Property has offers
    82
    Milton On Stour, Dorset
    • Sleeps33
    • Bedrooms14
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    This stunning historic manor nestles in the heart of Milton on Stour, Dorset. (Ref. 1026929)

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

    • 5% off - Fri 7th Mar 2025 to 30th Apr 2026

    3 nights from Sat 28th Nov £5028

    Book now
  • A street view of a cottage with brick and stone walls with bushes and flowers outside at Apple Tree Cottage in Shillingstone near Sturminster Newton
    26
    Shillingstone near Sturminster Newton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A cosy brick-and-flint terraced cottage, within the pretty Dorset village of Shillingstone. (Ref. 925256)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov £420

    Last booked yesterday
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  • A house with a deck and outdoor furniture at Mallows Byre in Yetminster
    53
    Yetminster, Dorset
    • 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 30th Nov £457

    Last booked yesterday
    Book now
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