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Helmsley • Dates • Guests
Helmsley • Dates • Guests

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£360
£1,500+
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Helmsley cottages

109 properties found
Chop Gate, near Stokesley, North Yorkshire

Black Cat Cottage - Chop Gate

4222

Our grading

7 nights

£596 - £1,081

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South Kilvington, near Thirsk, North Yorkshire

Grange View Cottage - Thirsk

4213

Our grading

7 nights

£738 - £1,205

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Osmotherley, near Northallerton, North Yorkshire

Clover Cottage Osmotherley

4222

Our grading

7 nights

£537 - £1,156

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Helmsley, North Yorkshire

Rose Cottage - Helmsley

633

Our grading

7 nights

£875 - £1,770

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Chop Gate, near Stokesley, North Yorkshire

The Granary At Cross Holme Farm

4222

Our grading

7 nights

£400 - £837

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Helmsley, Yorkshire

Linfitt - Helmsley

8442

Our grading

7 nights

£1,748 - £2,848

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Osmotherley, near Northallerton, North Yorkshire

Vane House Cottage

2111

Our grading

7 nights

£475 - £730

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Helmsley, Yorkshire

Cosy Barn - Helmsley

211

Our grading

7 nights

£528 - £929

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Helmsley, North Yorkshire

Primrose Garth

4211

Our grading

7 nights

£610 - £1,090

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Chop Gate, near Stokesley, North Yorkshire

Witches Cottage - Chop Gate

4221

Our grading

7 nights

£578 - £1,047

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Thimbleby, near Northallerton, North Yorkshire

Webstone Cottage

4212

Our grading

7 nights

£633 - £1,056

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Great Busby, near Stokesley, North Yorkshire

The Old Hay Barn

6313

Our grading

7 nights

£812 - £1,749

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Showing 1-12 of 109 properties

Helmsley holiday lets 

If you’re looking for a break in a setting of breathtaking beauty, investigate our Helmsley cottages collection in the magnificent North York Moors National Park. This glorious landscape is a great destination for a self-catering holiday, whether for nature and wildlife lovers seeking a peaceful retreat or an energetic family who loves outdoor adventures. Keen walkers, cyclists and horse riders are spoiled for choice, with miles of wonderful scenic trails across the hills and dales carpeted with heather. Charming market towns include Hemsley, with its medieval castle and Victorian walled garden, while historic Kirkbymoorside, known as the gateway to the moors, has held a weekly market for 750 years. Both towns have historic buildings, independent shops and traditional tea rooms offering fine Yorkshire fare. 

Less than 2 miles from Helmsley lie the atmospheric remains of historic Rievaulx Abbey. Once one of the greatest and most powerful abbeys in England, it remains a magnificent presence, in a beautifully tranquil setting. A stream runs through the village green in idyllic Hutton-le-Hole, where you’ll find the remarkable open-air Ryedale Folk Museum. Take a step back in time through the centuries, with exhibits that range from an Iron Age roundhouse and magnificent Manor House to a 1950s shop. The farming section houses rare pigs, sheep and chickens to feed. For a taste of sea and sand, jump aboard the heritage steam train from Pickering to the coast and golden beach at picturesque Whitby. Discover more about our fantastic line-up of Helmsley cottages above.