Short Breaks in Dorset

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Your search returned 477 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
    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

    3 nights from £402

    Last booked 2 days ago
    Book now
  • A wooden front door next to a window with shutters and a gray mailbox numbered 20 at Smugglers Cottage in Weymouth
    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

    3 nights from £643

    Last booked yesterday
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  • 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

    • 10% off - Fri 3rd Apr to 17th Apr 2026

    3 nights from £471

    Book now
  • A living room with two grey sofas and a wooden boat-shaped shelf with books at Chesil Retreat Weymouth
    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

    3 nights from £484

    Last booked 2 days ago
    Book now
  • A white cottage with a garden and wooden archway surrounded by a fence at Willowbrook Cottage in Litton Cheney
    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

    3 nights from £693

    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
    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

    3 nights from £1232

    Last booked 2 days ago
    Book now
  • An outdoor area with a ping pong table and a house at The Stable House in Sherborne
    51
    Sherborne, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Unwind in this stylish countryside retreat with a private, screened hot tub, cosy woodburner, pool table and spacious enclosed garden. (Ref. 1070465)

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

    3 nights from £1050

    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
    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

    3 nights from £507

    Last booked 2 days ago
    Book now
  • 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
    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

    3 nights from £532

    Book now
  • A wooden house with brick foundation surrounded by trees and plants at Willow Brook in Okeford Fitzpaine
    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

    3 nights from £584

    Book now
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