Winter Short Breaks in Dorset

REFINE SEARCH

Your search returned 472 cottages.

Most relevant
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Rating (lowest first)
  • Rating (highest first)
  • Location (A to Z)
  • Location (Z to A)
  • Property name (A to Z)
  • Property name (Z to A)
10
  • 10
  • 20
  • 50
  • 100
Map View
  • A patio with a round table and two chairs with two mugs on the table overlooking a gravel area and green hills at Burton Bay in Burton Bradstock
    20
    Burton Bradstock, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Pets welcome. (Ref. 994050)

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

    3 nights from Sun 30th Nov £475

    Secure your holiday with a 30% deposit* Book now
  • An exterior courtyard with stone buildings a staircase and no parking signs at George's House in Brewers Quay Harbour
    28
    Brewers Quay Harbour, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Four bedrooms in Kellaway Court, Weymouth. (Ref. 994219)

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

    3 nights from Fri 28th Nov £790

    Secure your holiday with a 30% deposit* Book now
  • A white semi detached house with blue doors and a blue fence under a clear sky at Ashwood Brewers Quay Harbour
    22
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Modern 3 Storey house. (Ref. 993939)

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

    3 nights from Fri 28th Nov £765

    Secure your holiday with a 30% deposit* Book now
  • A stone house with green garage doors and white windows next to a building with a boarded-up window at Swanage Driftwood in Swanage
    37
    Swanage, Dorset
    • Sleeps10
    • Bedrooms5
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Sleeps 10, large open plan living kitchen dining room. (Ref. 994706)

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

    3 nights from Sat 29th Nov £913

    Secure your holiday with a 30% deposit*
    Last booked 2 hours ago
    Book now
  • A living room with a wooden coffee table two patchwork chairs a fireplace and a window with an ocean view at Beach Retreat in Weymouth
    40
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A sea-front two-bedroom apartment fronting Weymouth bay, Dorset. (Ref. 1100406)

    • Wi-fi
    • Dishwasher

    3 nights from Sat 29th Nov £630

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A living room with a blue sofa and ottoman near a fireplace and television at Owls Rest in Weymouth
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A homely, mid-terrace cottage based in Weymouth. (Ref. 1094925)

    • Wi-fi
    • Off-road parking
    • Baby-friendly

    3 nights from Sat 29th Nov £440

    Secure your holiday with a 30% deposit* Book now
  • A blue two-story building with bay windows and white doors on a brick street at Tradewinds Brewers Quay Harbour
    17
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. (Ref. 994737)

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

    3 nights from Fri 28th Nov £714

    Secure your holiday with a 30% deposit* Book now
  • 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 Fri 28th Nov £566

    Secure your holiday with a 30% deposit* Book now
  • A stone building with a thatched roof and multiple windows along a street at Farrier's Lodge in Corfe Castle
    27
    Corfe Castle, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Stylish and contemporary cottage in the heart of Corfe Castle, Dorset. (Ref. 994182)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Fri 28th Nov £566

    Secure your holiday with a 30% deposit* Book now
  • A row of houses with a white picket fence and small garden in front at Smugglers Cottage in Christchurch
    Property has offers
    32
    Christchurch, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A pretty, one-bedroom cottage resting in Christchurch, Dorset. (Ref. 1098695)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 40% off - Thu 7th Aug to 31st Oct 2025

    3 nights from Mon 5th Jan £638

    Secure your holiday with a 30% deposit*
    Last booked 3 hours ago
    Book now
Most relevant
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Rating (lowest first)
  • Rating (highest first)
  • Location (A to Z)
  • Location (Z to A)
  • Property name (A to Z)
  • Property name (Z to A)
10
  • 10
  • 20
  • 50
  • 100
Map View

Quick links

Popular Destinations