Helmsley Romantic Accommodation

We selected the 1066 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights in Helmsley

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.

Woodland Glow

Woodland Glow

  • 5 guests

  • 3 bedrooms

Egton, Whitby

Get back to nature in this eye-catching timber lodge, set in wooded grounds near Whitby. A vaulted main living space and generous bedrooms make this home feel like an American log cabin.

Romancing the Stone

Romancing the Stone

  • 5 guests

  • 3 bedrooms

Crayke, York

This charming home in the heart of Yorkshire is a real escape from reality. A traditional stone cottage in the village of Crayke, it’s got bags of character, plenty of style and next-level comfort.

Tranquil Farmhouse

Tranquil Farmhouse

  • 6 guests

  • 3 bedrooms

Old Byland, York

Granary Cottage is a delightful farmhouse nestled on a working farm in the heart of the breathtaking North York Moors National Park. With its rustic charm and idyllic surroundings, this countryside retreat offers three spacious bedrooms, three bathrooms, a cosy living room, and a fully-equipped kitchen-diner.


We selected the top 3% holiday homes in Helmsley Romantic Accommodation

Explore the 1066 most perfect homes in our collection

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Most popular homes in Helmsley

The Stable Boy

The Stable Boy

  • 6 guests

  • 2 bedrooms

Saltburn-by-the-Sea, Redcar and Cleveland

Cozy Rose Retreat

Cozy Rose Retreat

  • 4 guests

  • 2 bedrooms

Pickering, North Yorkshire

Yorkshire Gem

Yorkshire Gem

  • 4 guests

  • 2 bedrooms

Kirkbymoorside, York

On The Market

On The Market

  • 4 guests

  • 2 bedrooms

Helmsley, York

Willow in Bloom

Willow in Bloom

  • 16 guests

  • 8 bedrooms

Rosedale East Side, North Yorkshire

Pat-a-Cake

Pat-a-Cake

  • 2 guests

  • 1 bedrooms

Pickering, North Yorkshire

The Daffodil Garden

The Daffodil Garden

  • 2 guests

  • 1 bedrooms

Scargill, Barnard Castle

Ivy & Sea Grass

Ivy & Sea Grass

  • 4 guests

  • 2 bedrooms

Whitby, North Yorkshire

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Frequently asked questions

Discover the most romantic accommodation in Helmsley. We’ve handpicked homes that are perfect for two, in soulful neighbourhood locations with characterful living spaces, sumptuous bedrooms and luxurious bathrooms. Book today and enjoy a short or extended stay in the most romantic accommodation that Helmsley has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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