Holiday Cottages in Helmsley

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Your search returned 44 cottages.

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  • The exterior of a stone and brick building with a wooden bench and potted plants next to a wooden barn at The Old Hayloft in Kirkbymoorside
    28
    Kirkbymoorside, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Yorkshire Coastal Cottages rating

    Homely barn conversion 3.5 miles from Kirkbymoorside in North Yorkshire. (Ref. 974773)

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

    7 nights from $550

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A stone house with a blue door and two chimneys seen from a garden with a stone path and green plants at Cliff House in Helmsley
    53
    Helmsley, Yorkshire Dales - North
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Yorkshire Coastal Cottages rating

    This quaint cottage lies in the market town, Hemlsley, North Yorkshire. (Ref. 1064092)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from $724

    Secure your holiday with a 30% deposit* Book now
  • 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

      4.8★

      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 $417

    Secure your holiday with a 30% deposit*
    Last booked 4 hours ago
    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 $783

    Secure your holiday with a 30% deposit* Book now
  • 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 $756

    Secure your holiday with a 30% deposit* Book now
  • A lodge with decking and glass railing at Isca Lodge - With Decking - Lodge 1 Wombleton
    Property has offers
    22
    Wombleton, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsYes

    • Yorkshire Coastal Cottages rating

    Isca Lodge – with Decking, a neat single-storey lodge near Wombleton and North York Moors National Park, boasts a private deck and open-plan design. (Ref. 1191239)

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

    • 25% off - Fri 21st Nov 2025 to 20th Mar 2026

    7 nights from $727

    Secure your holiday with a 30% deposit* Book now
  • 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

      4.7★

      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 $756

    Secure your holiday with a 30% deposit* Book now
  • An outdoor area with a brick building, table and chairs at Stable Cottage in Cawton near Hovingham
    19
    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 $406

    Secure your holiday with a 30% deposit* Book now
  • A stone house with a garden and picnic table at Wethercote Cottage Old Byland near Helmsley
    25
    Old Byland near Helmsley, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      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 $481

    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
    29
    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

    7 nights from $991

    Secure your holiday with a 30% deposit* Book now
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