Book Luxury Short Stay Rentals in Helmsley

We selected the 1066 homes worth renting in this location

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Age 1 to 12

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Home spotlights in Helmsley

Horse & Carriage

Horse & Carriage

  • 6 guests

  • 3 bedrooms

Ripon, North Yorkshire

Looking at this stunning home, it's hard to believe that it was once a coach house. This is a testament to the hard work and creativity that went into the recent renovation.

Peach Cobbler

Peach Cobbler

  • 6 guests

  • 3 bedrooms

Osmotherley, Northallerton

Set in the pretty village of Osmotherley, this charming stone cottage is the perfect spot for families and friends looking to explore the legendary North York Moors and beyond. You'll feel like you've walked into a Period Living magazine photo shoot as soon as you step foot inside this magical home.

Here's A Dream

Here's A Dream

  • 2 guests

  • 1 bedrooms

Wilstrop, York

Formerly a stonemason's workshop, who worked on local churches, schools and Ampleforth Abbey, this home has now been fully renovated for a comfortable stay. There's a wood burner in the double-height living room for cosy evenings in and a small courtyard for taking in the Yorkshire air.

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 Short Stay Rentals

Explore the 1066 most perfect homes in our collection

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Most popular homes in Helmsley

Tranquil Teeside Cottage

Tranquil Teeside Cottage

  • 4 guests

  • 2 bedrooms

Barnard Castle, England

Beneath the Marske

Beneath the Marske

  • 4 guests

  • 2 bedrooms

Marske-by-the-Sea, Redcar and Cleveland

Cozy Rose Retreat

Cozy Rose Retreat

  • 4 guests

  • 2 bedrooms

Pickering, North Yorkshire

Let's Walk By the River

Let's Walk By the River

  • 4 guests

  • 2 bedrooms

Hurworth-on-Tees, Darlington

The Yorkshire Retreat

The Yorkshire Retreat

  • 12 guests

  • 6 bedrooms

Kepwick, Thirsk

Whispering Pines Cottage

Whispering Pines Cottage

  • 4 guests

  • 2 bedrooms

Old Byland, York

The Ecclesiastic

The Ecclesiastic

  • 10 guests

  • 5 bedrooms

Witton Gilbert, Durham

Ivy & Gold

Ivy & Gold

  • 2 guests

  • 1 bedrooms

Richmond, North Yorkshire

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Frequently asked questions

Browse our curated collection of Short Stay Rentals in Helmsley. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Helmsley luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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