Winter Short Breaks in Dorset

Your search returned 499 cottages.

REFINE SEARCH
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

    How reviews work

    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • A house with red roof and red door behind grassy hill with trees at Rempstone Farmhouse in Corfe Castle
    29
    Corfe Castle, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Rempstone Farmhouse, a delightful, detached holiday home resting near Corfe Castle in Dorset. (Ref. 1155019)

    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Washing machine
    • Games room

    3 nights from Mon 30th Nov £921

    Book now
  • A brick townhouse with multiple windows and green hedges in front at Plain Sailing in Weymouth
    42
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. (Ref. 1153879)

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

    3 nights from Sun 29th Nov £624

    Last booked yesterday
    Book now
  • A modern two-story house with large triangular windows and a glass balcony railing at 5 Red Sails in Sandbanks
    50
    Sandbanks, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    5 Red Sails, a beautifully-presented home in the stunning neighbourhood of Sandbanks in Poole, Dorset. (Ref. 1151567)

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

    3 nights from Sun 29th Nov £1145

    Book now
  • A garden shed with a table and chairs in the garden at tbc
    Property has offers
    17
    Swanage, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

    • Dream Cottages rating

    Glamping cabin on the Jurassic Coast with breakfast is a simple, pet-friendly cabin near Swanage, Dorset, with studio layout, garden views and barbecue. (Ref. 1200463)

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

    3 nights from Sat 28th Nov was £466 £442

    Book now
  • Front view of a two-storey house with white framed windows and doors with flowering bushes in front at Chine Heights in Bournemouth
    32
    Bournemouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A duplex apartment resting in the coastal town of Bournemouth, Dorset. (Ref. 1133748)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov £651

    Book now
  • A window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour
    45
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. (Ref. 1107011)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov £448

    Book now
  • Stone house with wooden door and four windows and plants in front at Norden House in Maiden Newton
    29
    Maiden Newton, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A character filled property resting in the pretty village of Maiden Netwon in Dorset. (Ref. 1072294)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Sat 28th Nov £781

    Book now
  • An exterior view of a stone house with wooden windows and door on a gravel ground at The Stables Burton Bradstock
    31
    Burton Bradstock, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A beautifully presented property located in peaceful village of Burton Bradstock. (Ref. 1069215)

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

    3 nights from Sat 28th Nov £694

    Book now
  • An outdoor patio area with tables, chairs, and flower beds outside cream walls with blue doors and windows at The Compass in Swanage
    24
    Swanage, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Lovely apartment nestled in the thriving Dorest town of Swanage. (Ref. 979371)

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

    3 nights from Sun 29th Nov £367

    Last booked yesterday
    Book now
  • A house with a garage and plants in front at Millmead House Annex Portesham
    New property
    27
    Portesham, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

    • 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 £338

    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