Winter Short Breaks in Dorset

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    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 windows and a pathway at 1 Fernhill Avenue Weymouth
    62
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    Greenwell, a delightful house located in the town of Weymouth in Dorset boasting a Smart TV, woodburning stove and proximity to the beach and pub. (Ref. 1128598)

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

    3 nights from Sat 28th Nov $1316

    Book now
  • A small A-frame house with a wooden deck and stairs surrounded by trees and grass at Apple Tree Lodge in Gillingham
    23
    Gillingham, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Unique, A-frame lodge placed near Gillingham in Dorset. (Ref. 970181)

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

    3 nights from Mon 30th Nov $561

    Book now
  • A large two-story house with multiple sliding glass doors and windows and outdoor seating on a grassy yard at Shutts House Garden Apartment in Coombe Bissett
    32
    Coombe Bissett, Wiltshire
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Absolutely stunning, luxurious ground floor accommodation at the eastern end of Wiltshire's beautiful Chalke Valley. (Ref. 1016405)

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

    3 nights from Sat 28th Nov $1500

    Book now
  • Front of a white building with black door and window frames flowers in front at Harbour Reach Brewers Quay Harbour
    36
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Stylish fisherman’s cottage just a few minutes’ walk from Old Harbour in Weymouth. (Ref. 1058438)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 29th Nov $820

    Book now
  • A stone cottage with a wooden gate and a sign reading Salisbury Terrace surrounded by a garden at Jasmine Cottage in Kilmington Devon
    17
    Kilmington, Devon, Devon
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A traditional, pet-friendly, semi-detached cottage nestled in Kilmington, Devon. (Ref. 1096104)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Wed 6th Jan $401

    Book now
  • A row of yellow terraced houses with street lamps and paved walkways at Olympic Cottage in Portland
    22
    Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Modern and spacious cottage for couples or family in the Isle of Portland. (Ref. 994497)

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

    3 nights from Sun 29th Nov $843

    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
    Christchurch, Dorset
    • 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 - Mon 18th May to 25th Sep 2026

    3 nights from Sat 28th Nov $843

    Book now
  • A front entrance with a blue door and window at 23 The Maltings in Weymouth
    New property
    27
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Dolphin Cottage is a lovely cottage nestled into the bustling seaside town of Weymouth, Dorset, close to a shop, pub, local walks, and beaches. (Ref. 1179916)

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

    3 nights from Sat 28th Nov $871

    Last booked yesterday
    Book now
  • A row of colorful waterfront houses with windows and doors along a stone wall with wooden docks in front at Stanley House in Weymouth
    38
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Stanley House is an exceptional harbourside cottage located in the heart of Weymouth, Dorset. (Ref. 1138865)

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

    3 nights from Sat 28th Nov $1579

    Book now
  • A living room with a sofa and coffee table at 6 Bedford Place in Bridport
    New property
    30
    Bridport, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

    • Dream Cottages rating

    No. (Ref. 1159804)

    • Wi-fi
    • Washing machine

    3 nights from Sun 29th Nov $626

    Book now
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