Summer Breaks in Dorset

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Your search returned 515 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

      5.0★

      Perfect

    • 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 £707 £691

    Last booked 3 days ago
    Book now
  • A garden with flowering plants and shrubs in front of a stone building with a tiled roof at Middle Farm Annex in Long Bredy
    Property has offers
    40
    Long Bredy, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A detached barn conversion set within the village of Long Bredy. (Ref. 998739)

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

    7 nights from Sat 29th Aug was £1030 £990

    Last booked yesterday
    Book now
  • A white brick building with green framed windows a red post box a stone statue of a dog a garden with flowers and a red bicycle at Old Post Office Sherborne
    Property has offers
    46
    Sherborne, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    Old Post Office is a contemporary, four-bedroom home resting rurally in Glanvilles Wootton near Sherborne, Dorset. (Ref. 1129395)

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

    7 nights from Fri 21st Aug £2882

    Book now
  • A wooden front door next to a window with shutters and a gray mailbox numbered 20 at Smugglers Cottage in Weymouth
    Property has offers
    27
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A contemporary, three-storey property resting by the harbour in Weymouth, Dorset. (Ref. 1058500)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from Sat 29th Aug was £1095 £1079

    Last booked yesterday
    Book now
  • 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 £1029 £978

    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

    7 nights from Fri 17th Jul was £1254 £1212

    Last booked yesterday
    Book now
  • A view of rooftops with chimneys and a cliff by the sea at Seaview in Swanage
    58
    Swanage, Dorset
    • Sleeps7
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    This all-ground-floor cottage rests in the charming seaside resort of Swanage on the Jurassic Coast of Dorset. (Ref. 1012027)

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

    7 nights from Sat 29th Aug £1493

    Book now
  • A brick house with black doors and windows a bench and potted plants outside at Meadow View Barn in Bere Regis
    Property has offers
    29
    Bere Regis, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Charming, modern barn located in the Dorset village of Bere Regis. (Ref. 1000906)

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

    • 20% off - Fri 3rd Apr to 17th Apr 2026

    7 nights from Fri 5th Jun £846

    Book now
  • A wooden house with brick foundation surrounded by trees and plants at Willow Brook in Okeford Fitzpaine
    Property has offers
    12
    Okeford Fitzpaine, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    A well-presented barn conversion resting on the outskirts of Okeford Fitzpaine, Dorset. (Ref. 1137516)

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

    7 nights from Fri 5th Jun £1039

    Book now
  • A window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour
    45
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. (Ref. 1107011)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from Fri 7th Aug £997

    Book now
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