Holiday Cottages in Helmsley

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Your search returned 39 cottages.

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  • Exterior view of a two-story brick house with white framed windows and doors surrounded by a garden at Sunnyside Garden Cottage in Husthwaite
    11
    Husthwaite, North York Moors & Coast
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Yorkshire Coastal Cottages rating

    A spacious annexe cottage in the village of Hushtwaite in North Yorkshire. (Ref. 959719)

    • Wi-fi
    • Off-road parking
    • Games room

    7 nights from £312

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with a green front door surrounded by plants and flowers with a patio area at Cartwheel Cottage in Yearsley
    19
    Yearsley, North York Moors & Coast
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Yorkshire Coastal Cottages rating

    A charming ground floor annexe resting in Yearsley, North Yorkshire. (Ref. 1022390)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher

    7 nights from £570

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  • Stone cottage with a tiled roof a pale purple door and windows with plants and flowers outside at Grouse Cottage Low Hagg Farm near Kirkbymoorside
    15
    Low Hagg Farm near Kirkbymoorside, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Yorkshire Coastal Cottages rating

    Delightful stone cottage in courtyard, set in open countryside. (Ref. 929319)

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

    7 nights from £577

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  • A garden with outdoor wooden table and chairs surrounded by bushes and trees at Badger in Little Thirkleby near Thirsk
    23
    Little Thirkleby near Thirsk, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsNo

    • Yorkshire Coastal Cottages rating

    Badger is an elegant house in Little Thirkleby, North Yorkshire, boasting an enclosed garden, and access to a tennis court, swimming pool. (Ref. 1170004)

    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Washing machine
    • Baby-friendly

    7 nights from £938

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  • A stone cottage with two pale purple doors a gravel courtyard with metal table and chairs and plants at Partridge Cottage Low Hagg Farm near Kirkbymoorside
    18
    Low Hagg Farm near Kirkbymoorside, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • Yorkshire Coastal Cottages rating

    Cosy character cottage in wonderful rural position. (Ref. 929318)

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

    7 nights from £577

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  • A stone cottage with a red tiled roof and manicured garden at Ivy Cottage in Helmsley
    Property has offers
    24
    Helmsley, North York Moors & Coast
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Yorkshire Coastal Cottages rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    Lovely double-fronted cottage within a short stroll of the picturesque market town of Helmsley within the North Yorkshire National Park. (Ref. 947064)

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

    • 10% off - Sat 2nd Aug to 30th Aug 2025

    7 nights from £496

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  • A brick cottage with a tiled roof a patio door and potted plants with an outdoor table and chairs under an umbrella at Stable Cottage in Cawton near Hovingham
    17
    Cawton near Hovingham, Vale of York & Yorkshire Wolds
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8★

      Outstanding

    • Yorkshire Coastal Cottages rating

    Detached pet-friendly cottage near Hovingham. (Ref. 21723)

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

    7 nights from £304

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  • An outdoor area with a stone building with tiled roof multiple white doors and windows a raised stone patio with potted plants chairs and a bench on gravel at Norah's Nook in Farndale near Kirkbymoorside
    18
    Farndale near Kirkbymoorside, North York Moors & Coast
    • Sleeps3
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Yorkshire Coastal Cottages rating

    Detached attractive stone barn conversion in a peaceful location near Kirkbymoorside. (Ref. 911836)

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

    7 nights from £340

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  • A stone house with a red tiled roof and chickens on the dirt ground at Erica's 'eaven Farndale near Kirkbymoorside
    24
    Farndale near Kirkbymoorside, Vale of York & Yorkshire Wolds
    • Sleeps3
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Yorkshire Coastal Cottages rating

    Detached stone barn conversion in courtyard setting on owners' farm, near Kirkbymoorside. (Ref. 929845)

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

    7 nights from £337

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  • The exterior of a two story house with four windows and a blue door at Crumble's Cottage in Kirkbymoorside
    18
    Kirkbymoorside, North York Moors & Coast
    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Yorkshire Coastal Cottages rating

    A pretty, semi-detached cottage lying in Kirkbymoorside, North Yorkshire. (Ref. 1118132)

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

    7 nights from £374

    Secure your holiday with a 30% deposit* Book now
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