Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 92 cottages.

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  • Anvil Cottage

    Kirkbymoorside, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    A homely cottage nestled in the hub of Kirkbymoorside, on the edge of the North York Moors National Park. Town centre. WiFi. Helmsley 5.9 miles; Pickering 7.5 miles. (Ref. 1064915)

    • 10% off - Fri 7th May to 14th May 2021

    7 nights from £364

    Secure this property with a 30% deposit*
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  • Welburn Grange Farm

    Welburn near Kirkbymoorside, Vale of York & Yorkshire Wolds
    • Sleeps14
    • Bedrooms7
    • PetsYes
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    A spacious, detached property situated on a small holding in the village of Welburn. Ideal for families. Ample parking. WiFi. Kirkbymoorside 3.2 miles; Pickering 10.3 miles. (Ref. 1065690)

    7 nights from £1718

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  • Rednal Cottage

    Helmsley, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    This characterful Victorian mid-terrace rests in the market town of Helmsley in North Yorkshire. Three-storey. In the North York Moors National Park. Pet-friendly. Thirsk 14.2 miles; York 24.2 miles. (Ref. 1053977)

    7 nights from £321

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  • Mulberry Lodge

    Amotherby near Malton, North York Moors & Coast
    • Sleeps6
    • Bedrooms3
    • PetsNo
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    A contemporary wooden lodge, situated in Amotherby near Malton. Private decking with hot tub. Off-road parking. Close to Howardian Hills and North York Moors National Park. Malton 3.6 miles; York 20.1 miles. (Ref. 1062010)

    7 nights from £643

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  • 6 Church Street

    Kirkbymoorside, North York Moors & Coast
    • Sleeps8
    • Bedrooms4
    • PetsYes
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    A characterful stone-built property resting in the centre of Kirkbymoorside. Pet-friendly. WiFi. Woodburning stove. Pickering 7.6 miles; Scarborough 25 miles. (Ref. 1055794)

    7 nights from £526

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  • Ford End Cottage

    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 £422

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  • Gormire Cottage

    Sutton-under-Whitestonecliffe near Thirsk, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    A luxury, detached, stone barn conversion in Sutton-under-Whitestonecliffe near Thirsk, North Yorkshire. Woodburning stove. Pool table. Large shared garden. Thirsk 4.6 miles; Northallerton 12.7 miles. (Ref. 1052313)

    7 nights from £411

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  • Ivy Cottage

    Helmsley, North York Moors & Coast
    • Sleeps5
    • Bedrooms3
    • PetsNo
    • Sykes 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. WiFi. Lawned garden. Walks from the door. Kirkbymoorside 6 miles. (Ref. 947064)

    7 nights from £385

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  • Auburn House

    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 £596

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  • Summerfield Farm Cottage

    Helmsley, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    A charming, stone-built cottage resting on the outskirts of Helmsley. Pet-friendly. WiFi. Woodburning stove. Kirkbymoorside 5.3 miles. (Ref. 1016619)

    7 nights from £286

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  • Coronation Cottage

    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 £315

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  • The Old Potting Shed

    Kirkbymoorside, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    A characterful mid-terrace cottage in Kirkbymoorside in North Yorkshire. Exposed beams. Central location. Helmsley 5 miles. Pickering 6 miles. Scarborough 25.2 miles. Whitby 28 miles. (Ref. 980345)

    7 nights from £318

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  • Howe Green Cottage

    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 £365

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  • The Old School House

    Hutton-le-Hole, North York Moors & Coast
    • Sleeps5
    • Bedrooms3
    • PetsNo
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    Unique Grade II listed Old School House above shop overlooking village green in Hutton-le-Hole. First floor apartment with character window and enclosed rear courtyard. Modern open plan living. Helmsley 9 miles. (Ref. 932240)

    7 nights from £373

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  • The Cottage

    Thirsk, North York Moors & Coast
    • Sleeps2
    • Bedrooms1
    • PetsYes
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    A stone-built cottage which rests on the outskirts of Thirsk, North Yorkshire. Open-plan. WiFi. Just a moment’s walk from the Cleveland National Trail. York 27 miles. (Ref. 1004365)

    7 nights from £295

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  • Henhouse Cottage

    Gillamoor, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    A wonderful stone bungalow located in the village of Gillamoor, North Yorkshire. Open-plan. Woodburner. Open countryside views. Kirkbymoorside 2.7 miles; Pickering 11 miles. (Ref. 984261)

    7 nights from £414

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  • Brookleigh

    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 £397

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  • Witches Cottage

    Chop Gate near Helmsley, North York Moors & Coast
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    Stunning stone barn conversion in heart of North York Moors. All ground floor, open plan living, woodburner, granite work tops, underfloor heating. Excellent walking and cycling from the door. Helmsley 10 miles. (Ref. 931158)

    7 nights from £479

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  • School House Cottage

    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 £443

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  • Primrose Hill Farmhouse

    Hutton-le-Hole, North York Moors & Coast
    • Sleeps5
    • Bedrooms2
    • PetsYes
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    Delightful mid-terrace cottage in picture postcard Hutton-le-Hole. Rayburn, woodburning stove and lovely views over village green. WiFi, dog friendly. Kirbymoorside 3.5 miles. (Ref. 1401)

    7 nights from £330

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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.