Summer 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 living room with leather sofas glass coffee table and a television near large windows overlooking boats at Harbourside Haven Apartment 4 in Weymouth
    Property has offers
    20
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A stylish and contemporary apartment overlooking Weymouth Harbour in Dorset. (Ref. 1059265)

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

    7 nights from Sat 29th Aug $1428

    Book now
  • A garden shed with a table and chairs in the garden at tbc
    Property has offers
    17
    Swanage, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

    • Dream Cottages rating

    Glamping cabin on the Jurassic Coast with breakfast is a simple, pet-friendly cabin near Swanage, Dorset, with studio layout, garden views and barbecue. (Ref. 1200463)

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

    7 nights from Tue 1st Sep was $1214 $1147

    Book now
  • An outdoor area with a house, plants, and pathway at Brookfield Lodge in Drimpton
    Property has offers
    42
    Drimpton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Wheelchair friendly holiday cottage. (Ref. 967289)

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

    7 nights from Sat 29th Aug $819

    Book now
  • A patio with a table and chairs set outside a house with open glass doors and a large plant at Park Mews Weymouth
    Property has offers
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A stunning holiday home in the bustling seaside town centre of Weymouth in Dorset. (Ref. 1054948)

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

    7 nights from Sat 11th Jul $1372

    Book now
  • A living room with two black leather sofas, a wood-burning stove, a wooden coffee table, a floor lamp, a small TV on a wooden stand, and glass doors with orange curtains at The Old Cart Shed in Winterborne Stickland
    Property has offers
    37
    Winterborne Stickland, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Exceptional, spacious rural barn conversion. (Ref. 905897)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    • 10% off - Tue 5th May to 30th Jun 2026

    7 nights from Fri 5th Jun $1057

    Book now
  • An exterior view of a cottage with a wooden picnic table and umbrella on a paved patio at New Barn in Winterborne Stickland
    Property has offers
    33
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Lovely, well-appointed single-storey cottage near Winterborne Stickland. (Ref. 905896)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    7 nights from Fri 10th Jul $1116

    Last booked 2 days ago
    Book now
  • A stone cottage with a thatched roof and front door at Ivy Cottage in West Lulworth
    Property has offers
    35
    West Lulworth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Lovely thatched Grade II listed cottage for a family or friends. (Ref. 994302)

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

    7 nights from Sat 11th Jul $1878

    Book now
  • A small brick and stone building with a slate roof surrounded by trees and bushes in a garden at The Folly at Castlebridge in Mere
    Property has offers
    21
    Mere, Wiltshire
    • Sleeps2
    • Bedrooms1
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    Enchanting and unusual folly in an idyllic private setting. (Ref. 988942)

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

    7 nights from Fri 28th Aug $936

    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

    7 nights from Mon 15th Jun $4348

    Book now
  • A stone cottage with a glass conservatory and a garden with flowers and trees at Grazeland Cottage in Bridport
    Property has offers
    28
    Bridport, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    Perfect cottage to base yourself surrounded by the beautiful Dorset countryside. (Ref. 994231)

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

    7 nights from Sat 15th Aug $1171

    Book now
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