Book a stay in one of the best homes in Helmsley

We selected the 1066 homes worth renting in this location

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Home spotlights in Helmsley

Cherry Tree

Cherry Tree

  • 4 guests

  • 4 bedrooms

Helmsley, York

Packed with antiques collected over the years and grand yet striking rooms, this home in Hemsley is a real find. A red-brick facade and topiaried hedges set the tone as you arrive, and inside you’ll find a collection of hand-carved bureaus and cast iron bathtubs.

On The Market

On The Market

  • 4 guests

  • 2 bedrooms

Helmsley, York

Helmsley is a town drenched in unique attractions. A vibrant market selling chic items sits nearby to Michelin-star restaurants, showcasing the town's diversity.

On Heathered Moor

On Heathered Moor

  • 6 guests

  • 3 bedrooms

Helmsley, York

This pretty retreat is in the historic market town of Helmsley, sits on the edge of the North York Moors National Park. The 110 mile-long Cleveland Way National Trail begins in Helmsley and takes you through the heather-clad hills of the Moors to the cliffs and coast of Filey Brigg – a nine-day trek in total, but you can stop your car at any point along its length.

The Edge of the Meadow

The Edge of the Meadow

  • 8 guests

  • 4 bedrooms

Wilstrop, York

This delightful family home boasts wonderful views of Gilling Gap from the first-floor bedrooms. The home was originally owned by a family of stonemasons who worked on local churches, houses and schools – there’s a real sense of history here.


We selected the top 3% holiday homes in Helmsley

Explore the 1066 most perfect homes in our collection

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Most popular homes in Helmsley

Yorkshire Gem

Yorkshire Gem

  • 4 guests

  • 2 bedrooms

Kirkbymoorside, York

Box of Fudge

Box of Fudge

  • 4 guests

  • 2 bedrooms

Kirkbymoorside, York

Tranquil Farmhouse

Tranquil Farmhouse

  • 6 guests

  • 3 bedrooms

Old Byland, York

The Old Piggery

The Old Piggery

  • 2 guests

  • 1 bedrooms

Slingsby, York

Old Byland Hideaway

Old Byland Hideaway

  • 2 guests

  • 1 bedrooms

Old Byland, York

Here's A Dream

Here's A Dream

  • 2 guests

  • 1 bedrooms

Wilstrop, York

Cottage on the Hill

Cottage on the Hill

  • 4 guests

  • 2 bedrooms

Coneysthorpe, York

Whispering Pines Cottage

Whispering Pines Cottage

  • 4 guests

  • 2 bedrooms

Old Byland, York

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