Holiday Cottages in Helmsley

Your search returned 49 cottages.

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    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • Stone cottage facade with three doors and multiple windows on the front at Crooked Cottage in Kirkbymoorside
    Property has offers
    24
    Kirkbymoorside, North York Moors & Coast
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Yorkshire Coastal Cottages rating

    A charming, Grade II listed cottage on the edge of pretty Kirkbymoorside, Yorkshire. (Ref. 985142)

    • Pets go free
    • Wi-fi
    • Washing machine

    • 10% off - Wed 8th Jul to 31st Aug 2026

    7 nights from From £403

    Last booked 2 days ago
    Book now
  • A garden with a stone building and seating area at Cartwheel Cottage in Yearsley
    Property has offers
    19
    Yearsley, North York Moors & Coast
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Yorkshire Coastal Cottages rating

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

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher

    • 5% off - Mon 13th Jul to 30th Sep 2026

    7 nights from From £470

    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
    • Pet FriendlyNo

      4.5★

      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 From £569

    Last booked 7 hours ago
    Book now
  • A stone exterior wall with multiple doors and windows a chair and table on the patio with flower pots at The Byre in Thirsk
    29
    Thirsk, North York Moors & Coast
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Yorkshire Coastal Cottages rating

    A stone-built cottage resting on the outskirts of Thirsk. (Ref. 1002964)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher

    7 nights from From £359

    Book now
  • A garden with wooden table and chairs and plants in front of a stone house with large windows at The Granary in Appleton-le-Moors
    19
    Appleton-le-Moors, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Yorkshire Coastal Cottages rating

    Delightful detached stone cottage on owner's complex in Appleton-le-Moors village. (Ref. 936454)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Dishwasher

    7 nights from From £438

    Book now
  • 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
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Yorkshire Coastal Cottages rating

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

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

    7 nights from From £308

    Book now
  • A stone building with two green doors and a bench next to a pond with lily pads at The Cottage in Thirsk
    25
    Thirsk, North York Moors & Coast
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Yorkshire Coastal Cottages rating

    A stone-built cottage which rests on the outskirts of Thirsk, North Yorkshire. (Ref. 1004365)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher

    7 nights from From £359

    Book now
  • Front of a stone house with a wooden gate and fence with several potted plants on the ground at Stone Cross in Spaunton near Hutton-Le-Hole
    15
    Spaunton near Hutton-Le-Hole, North York Moors & Coast
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      5.0★

      Perfect

    • Yorkshire Coastal Cottages rating

    Beautiful stone cottage in the North York Moors National Park, close to the village of Hutton-le-Hole. (Ref. 975266)

    • Pets go free
    • Wi-fi
    • Ground floor bedroom
    • Washing machine
    • Baby-friendly

    7 nights from From £316

    Last booked yesterday
    Book now
  • A brick garage with an outdoor staircase and a seating area with a red umbrella at The Stables Crayke Lodge in Easingwold
    18
    Easingwold, Vale of York & Yorkshire Wolds
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Yorkshire Coastal Cottages rating

    Beautiful, first floor, studio-style cottage in rural location. (Ref. 917511)

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

    7 nights from From £319

    Book now
  • 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
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Yorkshire Coastal Cottages rating

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

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

    7 nights from From £319

    Book now
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