Holiday Cottages for October Half term

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Your search returned 453 cottages.

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  • A living room with blue sofas a wooden coffee table and red rug by large windows overlooking the sea at Weymouth Bay in Weymouth
    22
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A well-appointed apartment resting in Weymouth, Dorset. (Ref. 1003082)

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

    3 nights from Sat 25th Oct £656

    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

      4.7★

      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 Sat 25th Oct £566

    Secure your holiday with a 30% deposit* 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 Sun 26th Oct £532

    Secure your holiday with a 30% deposit* Book now
  • A living room with an orange armchair green sofa and ottoman wooden bookcase and hanging plants at Harbour Retreat in Weymouth
    23
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Harbour Retreat is a delightful three-storey cottage by the harbourside in Brewers Quay Weymouth, Dorset. (Ref. 1139963)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 26th Oct £524

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A house with a wooden door and windows next to a garden and trees at Tokenhill Cottage in Piddletrenthide
    44
    Piddletrenthide, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    This well-presented three-bedroom property resides in Piddletrenthide, Dorset. (Ref. 1130975)

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

    3 nights from Sat 1st Nov £741

    Secure your holiday with a 30% deposit* Book now
  • A brick cottage with a paved driveway a wooden door and a small lawn at Frome Lodge House in Frome Whitfield
    22
    Frome Whitfield, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    A charming, two-bedroom holiday home resting in Frome Whitfield, Dorset. (Ref. 1132783)

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

    3 nights from Fri 24th Oct £444

    Secure your holiday with a 30% deposit* Book now
  • A stone building facade with multiple windows flower boxes and a wrought iron fence at The Esplanade in Weymouth
    85
    Weymouth, Dorset
    • Sleeps18
    • Bedrooms9
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    The Esplanade is a stunning, nine-bedroom holiday dwelling residing in Weymouth, Dorset. (Ref. 1123341)

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

    3 nights from Mon 3rd Nov £2600

    Secure your holiday with a 30% deposit* Book now
  • A brick and white semi detached house with bay windows and potted plants outside at Anchor House Weymouth
    68
    Weymouth, Dorset
    • Sleeps15
    • Bedrooms6
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Anchor House is a stunning, pet-friendly townhouse with a private hot tub in the heart of Weymouth, Dorset, close to local amenities and the beach. (Ref. 1105510)

    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Mon 3rd Nov £1259

    Secure your holiday with a 30% deposit* Book now
  • A living room with two blue sofas a wooden coffee table a rug a TV a bookshelf and a fireplace at Ammonite Cottage Fortuneswell Portland
    32
    Fortuneswell Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Traditional Portland Cottage. (Ref. 993922)

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

    3 nights from Fri 24th Oct £515

    Secure your holiday with a 30% deposit* Book now
  • A backyard with a brick house a blue wooden shed a small fenced garden and plants at Sandpiper in Weymouth
    41
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A lovely one-bedroom holiday home resting in Weymouth, Dorset. (Ref. 1092449)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Dishwasher
    • Washing machine

    3 nights from Sat 25th Oct £480

    Secure your holiday with a 30% deposit* Book now
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