Luxury Long Stay Rentals in Helmsley

We selected the 1098 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.

The Salt Collector

The Salt Collector

  • 2 guests

  • 1 bedrooms

West Cliff, Whitby

In the centre of Whitby, this apartment puts a Blue Flag beach and narrow, medieval alleyways within easy walking distance. It’s a five-minute jaunt to the sprawling sands of Whitby Beach and you can even take the lift down the cliffs.

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.

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.


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

Explore the 1098 most perfect homes in our collection

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Most popular homes in Helmsley

The Woodlark

The Woodlark

  • 6 guests

  • 3 bedrooms

Sutton-on-the-Forest, York

Northern Orchid

Northern Orchid

  • 4 guests

  • 2 bedrooms

Saltburn-by-the-Sea, Redcar and Cleveland

Yorkshire Gem

Yorkshire Gem

  • 4 guests

  • 2 bedrooms

Kirkbymoorside, York

On Heathered Moor

On Heathered Moor

  • 6 guests

  • 3 bedrooms

Helmsley, York

Holly & Stone

Holly & Stone

  • 6 guests

  • 3 bedrooms

Pickering, North Yorkshire

The Yorkshire Retreat

The Yorkshire Retreat

  • 12 guests

  • 6 bedrooms

Kepwick, Thirsk

Charming Norton Hideaway

Charming Norton Hideaway

  • 4 guests

  • 2 bedrooms

Norton, Stockton-on-Tees

Beach Blues

Beach Blues

  • 2 guests

  • 1 bedrooms

Saltburn-by-the-Sea, Redcar and Cleveland

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Check upcoming rates & availability for Helmsley Long Stay Rentals


Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Helmsley. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Helmsley collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

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