Winter Short Breaks in Dorset

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  • A house with a garage and plants in front at Millmead House Annex Portesham
    27
    Portesham, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

    • Dream Cottages rating

    Millmead House Annex is a welcoming holiday annex in Portesham, Dorset, featuring open‑plan living, a woodburning stove and an enclosed garden. (Ref. 1201417)

    • Wi-fi
    • Off-road parking

    3 nights from Sat 28th Nov From $461

    Book now
  • Stone cottage exterior with multiple windows a dark wooden door potted plants and a small tree at Tick Tock Cottage in Marnhull
    30
    Marnhull, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Dream Cottages rating

    This fabulous Grade II listed cottage rests in the Dorset village of Marnhull. (Ref. 970616)

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

    3 nights from Mon 30th Nov From $556

    Book now
  • A stone cottage with black framed windows and a black door on a brick paved street at Stable Cottage Colyton
    27
    Colyton, Devon
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A Grade II listed former stable located in Colyton, in Devon, near to the Jurassic coast and beautiful countryside. (Ref. 1059490)

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

    3 nights from Mon 4th Jan From $526

    Book now
  • An outdoor area with seating and plants at Melanie's Cottage in Brewers Quay Harbour
    24
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Melanie's Cottage is a lovely mews-style holiday home located in Brewers Quay Harbour, Weymouth. (Ref. 1146011)

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

    3 nights from Sun 29th Nov From $871

    Book now
  • A white two-story house with bay windows and a dark front door at Bay Cottage in Weymouth
    49
    Weymouth, Dorset
    • Sleeps9
    • Bedrooms4
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Bay Cottage is a well-presented, three-storey detached house situated in the resort of Weymouth, Dorset. (Ref. 1139723)

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

    3 nights from Sun 3rd Jan From $1338

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  • A green house with satellite dish and plants at Driftmark in Weymouth
    New property
    25
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

    • Dream Cottages rating

    Driftmark is a pleasant, pet-friendly, four-storey cottage near the beach in Weymouth, Dorset, with open-plan living, an enclosed garden, and a barbecue. (Ref. 1205355)

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

    3 nights from Sat 28th Nov From $779

    Last booked 2 days ago
    Book now
  • A bungalow with a front yard at 7 Cedar Drive Preston
    36
    Preston, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      5.0★

      Perfect

    • Dream Cottages rating

    Cedar Drive is a charming house in Preston, Dorset, boasting ground-floor living, close proximity to local amenities and the coast for great days out. (Ref. 1173784)

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

    3 nights from Sun 3rd Jan From $674

    Book now
  • A mobile home with a deck and railing at Harbour View in Poole
    13
    Poole, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

    • Dream Cottages rating

    This beautiful lodge is situated on Haven's award-winning Rockley Park in Poole. (Ref. 1194016)

    • Off-road parking
    • Dishwasher
    • Washing machine

    3 nights from Sun 29th Nov From $632

    Book now
  • Exterior view of a building with black doors and windows a wooden picnic table and umbrella on a patio at Rowdens Barn in Winterborne Stickland
    36
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Beamed, single-storey holiday cottage near Winterborne Stickland. (Ref. 905898)

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

    3 nights from Sat 28th Nov From $535

    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
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Dream Cottages rating

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

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

    3 nights from Sat 28th Nov From $754

    Last booked 3 hours ago
    Book now
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