Book Luxury Short Stay Rentals in Helmsley

We selected the 1008 homes worth renting in this location

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Home spotlights in Helmsley

Charming Norton Hideaway

Charming Norton Hideaway

  • 4 guests

  • 2 bedrooms

Norton, Stockton-on-Tees

High Street, Norton is an expertly designed holiday home with style in abundance. Nestled in the heart of the market town of Norton, you'll be perfectly placed to enjoy the many independent restaurants, shops and bars nearby.

The Daffodil Garden

The Daffodil Garden

  • 2 guests

  • 1 bedrooms

Scargill, Barnard Castle

This charming Tudor castle, built in 1560, has been fully restored to create the perfect romantic retreat for two. Set in the picturesque Teesdale landscape, this historic property is located near the Yorkshire Dales and Lake District National Park, as well as the North Pennines Area of Outstanding Natural Beauty.

Yorkshire Enchantment

Yorkshire Enchantment

  • 14 guests

  • 7 bedrooms

Nether Silton, Thirsk

Immerse oneself in the restful charm of Nether Silton, making memories at this recently revitalised haven. Ascertain the elegance of interiors, possessing refinements that speak in a sophisticated whisper.

Pine Tree Chapel

Pine Tree Chapel

  • 6 guests

  • 2 bedrooms

Wilstrop, York

Nature fans will love unwinding at this gorgeous home in the heart of Yorkshire, situated just 200 yards from the southern edge of the beautiful North York Moors. With one of the UK’s most famous national parks on your doorstep, there are plenty of walking and cycling trails to be explored here.


We selected the top 3% holiday homes in Helmsley Short Stay Rentals

Explore the 1008 most perfect homes in our collection

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Most popular homes in Helmsley

Star of the Sea

Star of the Sea

  • 4 guests

  • 2 bedrooms

Saltburn-by-the-Sea, Redcar and Cleveland

Heathcliff, It's Me

Heathcliff, It's Me

  • 4 guests

  • 2 bedrooms

Guisborough, England

No Warmer Welcome

No Warmer Welcome

  • 24 guests

  • 11 bedrooms

Brotton, Saltburn-by-the-Sea

The Stable Boy

The Stable Boy

  • 6 guests

  • 2 bedrooms

Saltburn-by-the-Sea, Redcar and Cleveland

Tranquil Farmhouse

Tranquil Farmhouse

  • 6 guests

  • 3 bedrooms

Old Byland, York

Here's A Dream

Here's A Dream

  • 2 guests

  • 1 bedrooms

Wilstrop, York

Marine Parade

Marine Parade

  • 6 guests

  • 3 bedrooms

Saltburn-by-the-Sea, Redcar and Cleveland

Sweet Beams

Sweet Beams

  • 4 guests

  • 2 bedrooms

Brotton, Saltburn-by-the-Sea

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Check upcoming rates & availability for Helmsley Short Stay Rentals


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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