Summer Breaks in Dorset

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Your search returned 514 cottages.

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  • A small stone patio with a round table and chairs next to a wooden bench outside a stone house at Tiddlers Cottage in Uploders near Bridport
    Property has offers
    45
    Uploders near Bridport, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    This attractive, one-bedroom cottage resides in Uploders near Bridport, Dorset. (Ref. 1117867)

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

    7 nights from Mon 31st Aug was £698 £691

    Book now
  • A living room with two grey sofas and a wooden boat-shaped shelf with books at Chesil Retreat Weymouth
    Property has offers
    32
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A stylish property resting in the resort of Weymouth, Dorset. (Ref. 1100742)

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

    7 nights from Fri 19th Jun £915

    Book now
  • A garden with grass a wooden deck with a swing and a patio with chairs and a table at Blue Waters in Weymouth
    Property has offers
    25
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    A delightful, one-bedroom holiday home resting in Weymouth, Dorset. (Ref. 1133982)

    • Wi-fi
    • Dishwasher

    • 10% off - Fri 10th Apr to 23rd Apr 2026

    7 nights from Fri 17th Jul £1260

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  • A stone cottage with two windows a door and potted plants on a gravel yard with stone steps and greenery at Mill Cottage in Upwey
    Property has offers
    30
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A charming reverse-level cottage in the village of Upwey, Dorset. (Ref. 1072756)

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

    7 nights from Fri 14th Aug £936

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  • A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
    Property has offers
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. (Ref. 1133998)

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

    7 nights from Fri 7th Aug £1438

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  • A small A-frame house with a wooden deck and stairs surrounded by trees and grass at Apple Tree Lodge in Gillingham
    Property has offers
    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

    7 nights from Fri 19th Jun £770

    Book now
  • A corner seating area with two black armchairs near bay windows and a side table with a lamp at Two @ No36 in Weymouth
    Property has offers
    31
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Two @ No36, a wonderful, first-floor apartment situated in the heart of Weymouth in Dorset, with the beach on your doorstep. (Ref. 1162203)

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

    7 nights from Fri 28th Aug was £1038 £1033

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  • A bubbling outdoor hot tub next to a cream building with large green windows overlooking a gravel yard and countryside at The Hayloft in Stockland Honiton
    Property has offers
    43
    Stockland, Honiton, Devon
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    The Hayloft is a versatile, characterful, quirky, and Grade II-listed home, perfect for families or friends at Lower Lye, in the Blackdown Hills AONB. (Ref. 1120037)

    • Wi-fi
    • Electric car charging
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly

    7 nights from Fri 28th Aug was £975 £960

    Last booked 3 days ago
    Book now
  • A modern two story house with parking spaces and cars in front at Mary Bowes Terrace in Southbourne
    Property has offers
    30
    Southbourne, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A delightful, ground-floor apartment set in the seaside town of Southbourne. (Ref. 1125968)

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

    7 nights from Fri 12th Jun £782

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  • A white cottage with a garden and wooden archway surrounded by a fence at Willowbrook Cottage in Litton Cheney
    Property has offers
    28
    Litton Cheney, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    This beautifully-presented cottage rests in the village of Litton Cheney in Dorset. (Ref. 1021813)

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

    7 nights from Fri 28th Aug was £999 £978

    Book now
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