Winter Short Breaks in Dorset

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Your search returned 472 cottages.

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  • A wooden cabin with a balcony, outdoor seating, and a hot tub on a grassy area at Swan Lodge Castle Farm in Wedmore
    19
    Wedmore, Somerset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A high-quality, modern lodge sat on the outskirts of charming Wedmore in Somerset. (Ref. 983734)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher

    3 nights from Mon 1st Dec £678

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A stone house exterior with green door and lattice windows surrounded by garden at The Old School House in Piddletrenthide
    32
    Piddletrenthide, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    An attractive, converted Victorian school resting within Piddletrenthide. (Ref. 933650)

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

    3 nights from Sat 29th Nov £532

    Secure your holiday with a 30% deposit* Book now
  • A pink house with open double doors and a picnic table on a grass lawn with a stone wall and countryside beyond at Cliff Farm No 2 Cottage Burton Bradstock
    23
    Burton Bradstock, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A traditional farmhouse on the cliff top in Burton Bradstock, close to Hive Beach and it’s renowned café, West Bay, Wifi. (Ref. 994095)

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

    3 nights from Sat 29th Nov £413

    Secure your holiday with a 30% deposit* Book now
  • A waterfront with boats and buildings including Buccaneer Cottage at Brewers Quay Harbour
    23
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Pretty cottage in the heart of Weymouth. (Ref. 994047)

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

    3 nights from Sat 29th Nov £714

    Secure your holiday with a 30% deposit*
    Last booked 4 hours ago
    Book now
  • Exterior view of a brick building with balconies windows and surrounding garden at Ocean Watch 5 in Greenhill
    17
    Greenhill, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Modern, bright apartment with sea views over to Weymouth Bay. (Ref. 1098447)

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

    3 nights from Fri 28th Nov £670

    Secure your holiday with a 30% deposit* Book now
  • A stone and brick cottage with a tiled roof and a small garden beside a road at Way's Forge in Piddlehinton
    24
    Piddlehinton, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Located in countryside village of Piddlehinton, Way’s Forge is a lovely cosy holiday retreat. (Ref. 994768)

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

    3 nights from Sat 6th Dec £472

    Secure your holiday with a 30% deposit* Book now
  • 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 29th Nov £472

    Secure your holiday with a 30% deposit* Book now
  • A restaurant building with outdoor seating at The Beach Condo in Weymouth
    New property
    46
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms3
    • PetsNo

    • Dream Cottages rating

    The Beach Condo, a quaint duplex apartment over three floors, in the heart of Weymouth in Dorset features stunning sea vistas, and a nearby beach and pub. (Ref. 1176421)

    • Wi-fi
    • Dishwasher

    3 nights from Fri 28th Nov £911

    Secure your holiday with a 30% deposit* Book now
  • A stone and brick house with arched windows a green door a bench and gravel driveway at The Coach House at Lackington Farm in Piddletrenthide
    57
    Piddletrenthide, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Gold Gems Award Winner for Best on the South Coast 2023. (Ref. 1087048)

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

    3 nights from Fri 28th Nov £629

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A driveway with a silver van parked next to a house with a garage and trees at Redcliff View Lodge in Weymouth
    24
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    Sleeps six in Weymouth, patio garden. (Ref. 994586)

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

    3 nights from Fri 28th Nov £641

    Secure your holiday with a 30% deposit* Book now
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