Cottages in Helmsley

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  • Ford End Cottage

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    Ampleforth, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsYes
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    A lovely converted carriage shed dating back to the 18th century in the village centre of Ampleforth, North York Moors National Park. Underfloor heating. Woodburning stove. Village centre. Helmsley 4.9 miles; Rievaulx 7.5 miles; Kirkham Abbey 17.3 miles. (Ref. 1051110)

    7 nights from £419

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    Last booked 2 days ago
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  • Griff Lodge

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    Harome, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    A delightful, semi-detached bungalow resting in the pretty village of Harome in North Yorkshire. Ideal for two couples. Enclosed lawned garden. Helmsley 3 miles; Pickering 11.6 miles. (Ref. 1044119)

    7 nights from £304

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  • The Old Chapel

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    Thorgill near Kirkbymoorside, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsYes
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    A converted chapel resting in the peaceful hamlet of Thorgill near Kirkbymoorside. Countryside views. Within the North York Moors National Park. Large garden. Woodburning stove. Kirkbymoorside 9.1 miles; Pickering 11.9 miles. (Ref. 1051336)

    7 nights from £354

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  • 4 Castle Cottage

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    Husthwaite near Easingwold, North York Moors & Coast
    • Sleeps3
    • Bedrooms2
    • PetsNo
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    Charming traditional cottage in the quiet village of Husthwaite near Easingwold in the North Yorkshire. Original features. WiFi. Front and rear garden. Easingwold 5.3 miles; York 17.4 miles. (Ref. 1043214)

    7 nights from £317

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  • School House Cottage

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    Coxwold near Ampleforth, North York Moors & Coast
    • Sleeps2
    • Bedrooms1
    • PetsYes
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    A delightful couple's cottage resting in the conservation village of Coxwold in North Yorkshire. In the North York Moors National Park. Woodburning stove. WiFi. Next to tearooms. Thirsk 8 miles; York 18.3 miles. (Ref. 1044706)

    7 nights from £337

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  • 8 Pottergate Mews

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    Helmsley, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    Ideal for a family holiday in the heart of market town. Front garden and rear courtyard. WiFi. Thirsk 14 miles. (Ref. 956799)

    7 nights from £517

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  • Coronation Cottage

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    Helmsley near Kirkbymoorside, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    Charming stone cottage in the centre of Helmsley, North Yorkshire. All ground floor. Wet room. Pretty courtyard garden. Quietly tucked away, yet with plenty of amenities on the doorstep. Pickering 14 miles. (Ref. 26954)

    7 nights from £310

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  • Auburn House

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    Beadlam near Helmsley, North York Moors & Coast
    • Sleeps8
    • Bedrooms4
    • PetsNo
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    Beautiful period property in village location. Ensuite bathroom. TV with Freeview. Lovely garden. Ample off road parking. Village location with pub and restaurant. Helmsley 3 miles. (Ref. 943848)

    7 nights from £526

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  • Brookleigh

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    Hutton-le-Hole, North York Moors & Coast
    • Sleeps5
    • Bedrooms3
    • PetsYes
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    Charming, stone, period cottage in pretty village of Hutton-le-Hole. Open fire, cosy, comfortable accommodation. Private rear garden, lovely views over village green. Walkers' delight. Kirkbymoorside 3.5 miles. (Ref. 22745)

    7 nights from £393

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  • Ryedale Country Lodges - Hazel Lodge

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    Kirkbymoorside, North York Moors & Coast
    • Sleeps5
    • Bedrooms3
    • PetsYes
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    A superb, detached lodge resting on the outskirts of Kirkbymoorside. All-ground-floor. WiFi. Pet-friendly. Pickering 7.8 miles; Scarborough 25.4 miles. (Ref. 1011649)

    7 nights from £382

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  • Howe Green Cottage

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    Kirkbymoorside, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    Exceedingly pretty, detached stone cottage, a short walk from centre of Kirkbymoorside. Beamed ceilings, open fire. National Park and Heritage Coast within easy driving distance. Pickering 6 miles. (Ref. 1034138)

    7 nights from £315

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  • Hill Top

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    Hovingham, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsYes
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    This charming semi-detached cottage is situated in the village of Stonegrave, in North Yorkshire. WiFi. En-suite. Woodburner. (Ref. 989054)

    7 nights from £387

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  • Owl Cottage

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    Chop Gate near Helmsley, North York Moors & Coast
    • Sleeps2
    • Bedrooms1
    • PetsYes
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    Cosy stone barn conversion in rural countryside between Helmsley and Stokesley. All ground floor, open plan, one king-size bedroom. WiFi. Pet-friendly. Superb walking, cycling and touring area. Helmsley 10 miles. (Ref. 931157)

    7 nights from £297

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  • The Green

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    Lastingham near Kirbymoorside, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsYes
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    Country detached cottage located in the village of Lastingham. Woodburning stove and piano. Countryside views. Kirkbymoorside 5.3 miles. (Ref. 947541)

    7 nights from £427

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  • Castle View

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    Helmsley near Kirkbymoorside, North York Moors & Coast
    • Sleeps6
    • Bedrooms4
    • PetsYes
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    Magnificent semi-detached property in market town of Helmsley. Beautifully presented and well-equipped. Open fire, conservatory, delightful garden. Close to all amenities. (Ref. 2779)

    7 nights from £627

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On the border of the North York Moors National Park, this delightful market town is a haven for walkers and lovers of the outdoors.

Why Helmsley?

After an action-packed day among the wonders of the North York Moors, our Helmsley cottages enjoy close proximity to the town's charming pubs and delightful tea rooms to recharge the batteries. There is a selection of excellent independent shops and a weekly market along its attractive streets to pick up some of the finest local produce. From your Helmsley accommodation, be sure to explore the stunning Helmsley Castle and sculpture garden, as well as Duncombe Park and the National Centre for Birds of Prey for nature enthusiasts.

Places to Visit near Helmsley

Our range of cottages in Helmsley rest on the southern fringes of the North York Moors National Park, perfectly based for a break filled with activity and adventure. This National Park hugging the coast of Yorkshire has much to offer, not least its wide range of walks and cycle paths taking in some of the finest landscape scenery imaginable. Discover a handful of unique villages in and around the spectacular moors, waiting to be explored with rustic inns and delightful cafés offering those mid-adventure refreshments. Make your Helmsley cottage holiday a memorable one by visiting popular spots such as Ampleforth, Hutton-le-Hole, Kirkbymoorside, Pickering, Ripon and Thirsk.

Types of Holidays

All types of holidays can be enjoyed across Yorkshire with Sykes, whether you're seeking a Yorkshire cottage by the sea, or more of a rural retreat at a cottage in the Yorkshire countryside. Bring your dog along to enjoy the sublime walking country nearby by booking a North York Moors pet-friendly cottage, or really treat yourselves to a break in a Yorkshire luxury cottage.