Autumn Breaks in Dorset

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Your search returned 339 cottages.

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  • An outside view of a small brick building with a red door and a window with plants and a green utility box at Fountain Cottage in Weymouth
    16
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A cosy stone cottage for two this is the ideal place to spend quality time together, walking and exploring the local area. (Ref. 994208)

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

    3 nights from Mon 15th Dec €569

    Secure your holiday with a 30% deposit* Book now
  • A harbor with boats docked near buildings and a raised drawbridge at Harbours Edge in Brewers Quay Harbour
    27
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    Perfectly located on the harbour side in the heart of Weymouth. (Ref. 994172)

    • Wi-fi
    • Washing machine

    3 nights from Mon 15th Dec €488

    Secure your holiday with a 30% deposit* Book now
  • The Old Post Office - 1127439 - photo 1
    Property has offers
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

    • Dream Cottages rating

    The Old Post Office, a stylish pet-friendly house nestled in the town Weymouth, Dorset, features a Smart TV, proximity to the beach and marina. (Ref. 1127439)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 10% off - Sat 20th Dec to 27th Dec 2025

    3 nights from Mon 15th Dec €568

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of a brick building with multiple doors and windows and potted plants on gravel at The Apple Shed in Motcombe
    23
    Motcombe, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A homely cottage situated near the village of Motcombe, Dorset. (Ref. 957189)

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

    3 nights from Mon 15th Dec €551

    Secure your holiday with a 30% deposit* Book now
  • A garden with red roses and a metal chair beside a brick house at The Corner House in Weymouth
    39
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    The Corner House is a delightful terrace home resting in the popular seaside town of Weymouth, Dorset. (Ref. 1129331)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Mon 15th Dec €635

    Secure your holiday with a 30% deposit* Book now
  • A row of attached houses with one blue house covered in climbing plants and flowers in front at Fenders Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Delightful terraced cottage. (Ref. 998253)

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

    3 nights from Mon 15th Dec €665

    Secure your holiday with a 30% deposit* 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

      4.1★

      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 Mon 15th Dec €731

    Secure your holiday with a 30% deposit* Book now
  • A living room with a TV cabinet, armchair, ottoman, fireplace, and dining table with chairs at Quarrier's Rest in Swanage
    32
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    This charming, two-bedroom holiday home rests in Swanage, Dorset. (Ref. 1124578)

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

    3 nights from Mon 15th Dec €602

    Secure your holiday with a 30% deposit* Book now
  • An exterior view of a multi-story residential building with balconies and large windows at Townbridge Apartment in Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. (Ref. 1111030)

    • Wi-fi
    • Dishwasher

    3 nights from Mon 15th Dec €713

    Secure your holiday with a 30% deposit* Book now
  • A window seat with two mugs and a muffin on a tray overlooking a carousel and seaside at Shore View in Weymouth
    55
    Weymouth, Dorset
    • Sleeps10
    • Bedrooms5
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. (Ref. 1118900)

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

    3 nights from Mon 15th Dec €1284

    Secure your holiday with a 30% deposit* Book now
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