Holiday Cottages in Helmsley

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Your search returned 39 cottages.

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  • A stone house with a tiled roof and brown doors and windows with flower pots and a picnic bench on a lawn at Wethercote Cottage in Old Byland near Helmsley
    15
    Old Byland near Helmsley, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Yorkshire Coastal Cottages rating

    One of our farm based Yorkshire cottages, with lovely views over the moors, 7 miles from the market town of Helmsley. (Ref. 3626)

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

    7 nights from $487

    Secure your holiday with a 30% deposit* Book now
  • A stone house with white framed windows and a wooden bench on grass in front at The Green in Lastingham
    Property has offers
    28
    Lastingham, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Yorkshire Coastal Cottages rating

    The Green is a detached cottage located in the village of Lastingham near Kirkbymoorside, North Yorkshire. (Ref. 1134717)

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

    • 10% off - Fri 4th Jul to 11th Jul 2025

    7 nights from $946

    Secure your holiday with a 30% deposit* Book now
  • A stone house with a tiled roof and a small garden with a table and two chairs at 8 Pottergate Mews in Helmsley
    27
    Helmsley, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Yorkshire Coastal Cottages rating

    Ideal for a family holiday in the heart of market town. (Ref. 956799)

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

    7 nights from $794

    Secure your holiday with a 30% deposit* Book now
  • Brookleigh - 22745 - photo 1
    33
    Hutton-le-Hole, North York Moors & Coast
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • Yorkshire Coastal Cottages rating

    Charming, stone, period cottage in pretty village of Hutton-le-Hole. (Ref. 22745)

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

    7 nights from $551

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A stone house with tiled roof and white doors and windows with an outdoor bench at Cliff Cottage in Thirsk
    34
    Thirsk, North York Moors & Coast
    • Sleeps8
    • Bedrooms4
    • PetsYes

      3.7★

      Good

    • Yorkshire Coastal Cottages rating

    Cliff Cottage is a beautiful detached property in Boltby near Thirsk, North Yorkshire. (Ref. 1143122)

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

    7 nights from $989

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of a row of brick and stone houses with windows and doors on a street at Howe End Cottage in Kirkbymoorside
    21
    Kirkbymoorside, North York Moors & Coast
    • Sleeps4
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

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

    Cosy town house in heart of Kirkbymoorside. (Ref. 17787)

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

    7 nights from $869

    Secure your holiday with a 30% deposit* Book now
  • A stone facade of a residential building with multiple windows and two front doors
    27
    Rosedale Abbey, Yorkshire Dales - North
    • Sleeps9
    • Bedrooms5
    • PetsNo

    • Yorkshire Coastal Cottages rating

    The Old Post Office is a charming five-bedroom house in Rosedale Abbey, in the heart of the North York Moors National Park. (Ref. 1166944)

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

    7 nights from $1070

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A stone cottage with blue window frames and a wooden picnic table in a gravel courtyard at Foxglove Cottage in Harome
    11
    Harome, North York Moors & Coast
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.3★

      Good

    • Yorkshire Coastal Cottages rating

    A snug ground-floor cottage tucked away in the quiet village of Harome near Beadlam in North Yorkshire. (Ref. 1069744)

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

    7 nights from $809

    Secure your holiday with a 30% deposit* Book now
  • A wooden cabin with a porch surrounded by trees and grass at Chloes Lodge in Middleton Ryedale
    24
    Middleton, Ryedale, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Yorkshire Coastal Cottages rating

    A welcoming, detached lodge resting in Cropton near Middleton, North Yorkshire. (Ref. 1003270)

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

    7 nights from $752

    Secure your holiday with a 30% deposit* Book now
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