Book Luxury Holiday Rentals in Helmsley

Award-winning homes from £98

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Home spotlights in Helmsley

Cottage on the Hill

Cottage on the Hill

  • 4 guests

  • 2 bedrooms

Coneysthorpe, York

It's not every day you get to stay in a home dating back to the 18th century. However, this stone cottage in the Castle Howard Estate village of Coneysthorpe invites guests to do just that.

Rural Heart

Rural Heart

  • 6 guests

  • 3 bedrooms

Appleton East and West, North Yorkshire

This cosy home provides a true countryside escape. It's located on the cusp of Wensleydale and resides near the stretching natural beauty of the Yorkshire Dales.

Marine Parade

Marine Parade

  • 6 guests

  • 3 bedrooms

Saltburn-by-the-Sea, Redcar and Cleveland

Rejuvenate with panoramic coastal views and sea air at this contemporary home perched along the mighty beach cliffs of Saltburn-by-the-Sea. With the Victorian spa town's golden sands and bustling town centre all just a five-minute jaunt away, it's hard to imagine a better location.

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 Holiday Rentals

Explore the 1012 most perfect homes in our collection

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Most popular homes in Helmsley

Cherry Tree

Cherry Tree

  • 4 guests

  • 4 bedrooms

Helmsley, York

Osmund's Firewood

Osmund's Firewood

  • 8 guests

  • 4 bedrooms

Osmotherley, Northallerton

Yorkshire Enchantment

Yorkshire Enchantment

  • 14 guests

  • 7 bedrooms

Nether Silton, Thirsk

The Daffodil Garden

The Daffodil Garden

  • 2 guests

  • 1 bedrooms

Scargill, Barnard Castle

A Day At The Beach

A Day At The Beach

  • 8 guests

  • 4 bedrooms

Whitby, North Yorkshire

Pine Tree Chapel

Pine Tree Chapel

  • 6 guests

  • 2 bedrooms

Wilstrop, York

Yorkshire Gem

Yorkshire Gem

  • 4 guests

  • 2 bedrooms

Kirkbymoorside, York

Romancing the Stone

Romancing the Stone

  • 5 guests

  • 3 bedrooms

Crayke, York

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Helmsley. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Helmsley has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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