Winter Short Breaks in Dorset

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Your search returned 326 cottages.

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  • A single story house with a tiled roof a chimney and an antenna on a lawn at Broadstones in Bridport
    37
    Bridport, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A pleasant, detached bungalow resting in Bettiscombe outside Bridport, Dorset. (Ref. 1105472)

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

    3 nights from Sun 1st Mar £533

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  • A brick house exterior with white framed windows a door a mailbox and a small outdoor table with a bench at Goliath in Brewers Quay Harbour
    24
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Beautiful 1 bedroom stable conversion in the heart of the harbour area in Weymouth. (Ref. 1096825)

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

    3 nights from Sun 1st Mar £525

    Last booked yesterday
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  • An apartment building with multiple floors at Flat 13, Chesil House in Bridport
    33
    West Bay, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      3.8★

      Good

    • Dream Cottages rating

    Beachcombers, 13 Chesil House, a neat first-floor apartment in West Bay, Dorset, boasting beach views, and is near the pub, river, harbour and shop. (Ref. 1174085)

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

    3 nights from Sun 1st Mar £405

    Last booked yesterday
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  • A living room with a TV on a white stand and a black sofa with animal print cushions at Sunny Days in Weymouth
    24
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Modern refurbished terraced cottage in Weymouth, sleeping 4, short walk to the beach and town, WiFi, Off road parking for 1 car. (Ref. 994696)

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

    3 nights from Mon 2nd Mar £535

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  • A two-story corner house with a pink brick exterior and a bay window at Mermaid House in Brewers Quay Harbour
    41
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This stylish and neat holiday home rests in Brewers Quay Harbour in Weymouth, Dorset. (Ref. 1093760)

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

    3 nights from Tue 3rd Mar £686

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  • A marina with boats and yachts docked and buildings in the background at Harbourside Haven Apartment 1 in Weymouth
    18
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A superb first-floor apartment resting in Weymouth, Dorest. (Ref. 1059262)

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

    3 nights from Wed 4th Mar £730

    Last booked yesterday
    Book now
  • A blue painted two storey building with bay windows and white doors with black railings in front at Harbour Watch Apartment 1 Brewers Quay Harbour
    23
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    A lovely apartment perfect for couples in Weymouth. (Ref. 994289)

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

    3 nights from Sun 1st Mar £610

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  • A brick cottage with a paved driveway a wooden door and a small lawn at Frome Lodge House in Frome Whitfield
    22
    Frome Whitfield, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    A charming, two-bedroom holiday home resting in Frome Whitfield, Dorset. (Ref. 1132783)

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

    3 nights from Sun 1st Mar £477

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  • Boats docked in a harbor in front of buildings including Old Coastguard Apartment 2 in Weymouth
    Property has offers
    30
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    On Weymouth Harbourside this is an extraordinarily spacious apartment, sleeps 8, tastefully renovated, Large en-suite showers to all rooms, harbour views, WiFi. (Ref. 994463)

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

    • 15% off - Mon 23rd Feb to 2nd Apr 2026

    3 nights from Sun 1st Mar £1006

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  • A small blue house with patio furniture and potted plants on a tiled patio at Outlook Lodge in Bowleaze
    Property has offers
    28
    Bowleaze, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A lodge sleeping four people, Bowleaze area of Weymouth. (Ref. 994500)

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

    • 10% off - Sat 28th Feb to 14th Mar 2026

    3 nights from Sun 1st Mar £690

    Book now
Most relevant
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