Winter Short Breaks in Dorset

REFINE SEARCH

Your search returned 480 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
  • A living room with two black sofas a television and a glass door leading to an outdoor patio at 23 Millhams Street Christchurch
    26
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    23 Millhams Street, a stunning renovated Victorian cottage resting in the town of Christchurch in Dorset, close to a shop, a pub, and a beach. (Ref. 1162980)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Tue 2nd Dec £537

    Secure your holiday with a 30% deposit* Book now
  • A two-story brick house behind a stone and brick wall with a black gate and a tree nearby at The Nook in Weymouth
    40
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4

      Good

    • Dream Cottages rating

    The Nook is a charming, pet-friendly cottage resting near the beach in the town of Weymouth in Dorset, boasting a woodburning stove and enclosed garden. (Ref. 1107935)

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

    3 nights from Thu 1st Jan £494

    Secure your holiday with a 30% deposit* Book now
  • A balcony with wicker chairs a table and glass panels overlooking a harbor at Bears Apartment in Castletown Portland
    27
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5

      Outstanding

    • Dream Cottages rating

    A well-positioned, fourth-floor apartment resting in Castletown, Dorset. (Ref. 1119638)

    • Wi-fi
    • Swimming pool
    • Dishwasher
    • Washing machine

    3 nights from Mon 1st Dec £536

    Secure your holiday with a 30% deposit*
    Last booked 8 hours ago
    Book now
  • A three story house with a beige exterior stone and concrete walls at Osprey House Portland
    27
    Save £60 with code BFDEAL60
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    Detached, large and modern house for large group of friends or big family. (Ref. 994499)

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

    3 nights from Mon 1st Dec £714

    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
    Save £60 with code BFDEAL60
    • 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
    • 30% off - Sat 1st Nov 2025 to 28th Feb 2026

    3 nights from Wed 3rd Dec £442

    Secure your holiday with a 30% deposit* Book now
  • A house exterior with garage doors and flower pots at 8 Church Road Ferndown
    28
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    The Retreat is a fantastic house in Ferndown, Dorset, boasting an outdoor hot tub, open-plan living, Velux windows and a Smart TV with Sky. (Ref. 1179091)

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

    3 nights from Mon 1st Dec £639

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • Exterior of a single-story building with a green door wooden framed windows a metal ramp and a plant in a pot at Honey Bee Retreat in Tytherleigh
    34
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms1
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    A beautiful semi-detached barn conversion resting in Tytherleigh, Devon. (Ref. 1045057)

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

    3 nights from Fri 6th Mar £630

    Secure your holiday with a 30% deposit* Book now
  • A restaurant building with outdoor seating at The Beach Condo in Weymouth
    46
    Save £60 with code BFDEAL60
    • 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 Mon 1st Dec £911

    Secure your holiday with a 30% deposit* Book now
  • A backyard patio with a glass table and chairs purple flowers a wooden bench and a wooden swing at Anchors Away in Weymouth
    34
    Save £60 with code BFDEAL60
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    A wonderful three-storey holiday cottage settled in the seaside resort of Weymouth in Dorset. (Ref. 1096129)

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

    3 nights from Fri 5th Dec £689

    Secure your holiday with a 30% deposit* Book now
  • The front exterior of a brick house with several windows a wooden door and a white garage door at Mariners Rest in Weymouth
    15
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    Set in a lovely and quiet residential area of Weymouth, the house is a comfortable getaway for a family. (Ref. 994377)

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

    3 nights from Sat 20th Dec £592

    Secure your holiday with a 30% deposit* 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