Winter Short Breaks in Dorset

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    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • A three story house with a beige exterior stone and concrete walls at Osprey House Portland
    27
    Portland, Dorset
    • 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 Sun 29th Nov $985

    Book now
  • A front view of a large brick and white house with bay windows and a small porch at Dream View in Greenhill
    24
    Greenhill, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Located on the Esplanade in Weymouth with far reaching beach and sea views and within walking distance of the Harbour and town amenities. (Ref. 994167)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 29th Nov $803

    Last booked yesterday
    Book now
  • A living room with a sofa armchair wooden chest coffee table dining table and plants at Beach Side in West Bay
    26
    West Bay, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A delightful, ground-floor apartment resting in West Bay, Dorset. (Ref. 1095399)

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

    3 nights from Sat 28th Nov $622

    Book now
  • The exterior entrance of a white building with potted plants and stone wall at The Town House in Dorchester
    42
    Dorchester, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A charming townhouse set over three floors in the centre of Dorchester. (Ref. 1077743)

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

    3 nights from Sun 29th Nov $1129

    Book now
  • A mobile home with a deck and steps at Foxglove 4 Ringwood
    Property has offers
    29
    Oakdene Forest Park near Ferndown, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

    • Dream Cottages rating

    Foxglove 4, a agreeable caravan in Oakdene Forest Park near Ferndown, Dorset, has an open-plan layout and on-site facilities including a swimming pool. (Ref. 1205040)

    • Wi-fi
    • Ground floor bedroom

    • 20% off - Mon 15th Jun to 31st Oct 2026

    3 nights from Sat 28th Nov $644

    Book now
  • A brick residential building with multiple windows a gated entrance and a small staircase at Ocean Watch 1 in Greenhill
    20
    Greenhill, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Modern one level apartment. (Ref. 994505)

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

    3 nights from Sun 29th Nov $806

    Book now
  • A living room with two black sofas a television and a glass door leading to an outdoor patio at 23 Millhams Street Christchurch
    26
    Christchurch, Dorset
    • 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 Sat 28th Nov $721

    Book now
  • A coastal landscape with a building on grassy land overlooking the sea at Siesta Chalet in Eype Mouth Chalet Park
    30
    Eype Mouth Chalet Park, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A single-storey chalet in a wonderful location on the Eype Holiday Park, Dorset. (Ref. 1134626)

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

    3 nights from Mon 30th Nov $609

    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 Sun 29th Nov $985

    Book now
  • A stone cottage with black framed windows and a black door on a brick paved street at Stable Cottage Colyton
    27
    Colyton, Devon
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A Grade II listed former stable located in Colyton, in Devon, near to the Jurassic coast and beautiful countryside. (Ref. 1059490)

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

    3 nights from Sun 29th Nov $536

    Last booked yesterday
    Book now
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