Luxury Long Stay Rentals in Helmsley

We selected the 1066 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.

Yorkshire Homestead

Yorkshire Homestead

  • 16 guests

  • 8 bedrooms

East Heslerton, Malton

Set in one of the most beautiful parts of Yorkshire, this formerly derelict barn was chanced across by its owners in 2015, and lovingly converted into the stunning home it is today. The vibe is English country, with real moments of grandeur.

Osmund's Firewood

Osmund's Firewood

  • 8 guests

  • 4 bedrooms

Osmotherley, Northallerton

Set within the North York Moors National Park, the village of Osmotherley is a quaint resting spot for hikers and history fans. As this fantastic home is located just a four-minute drive from the Mount Grace Priory House and Gardens, you might fancy spending the day roaming the ruins of a medieval monastery.

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 1066 most perfect homes in our collection

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Most popular homes in Helmsley

Seashells by the Seashore

Seashells by the Seashore

  • 12 guests

  • 6 bedrooms

Whitby, North Yorkshire

Blackberry Cobbler

Blackberry Cobbler

  • 4 guests

  • 2 bedrooms

Haworth, Keighley

The Edge of the Meadow

The Edge of the Meadow

  • 8 guests

  • 4 bedrooms

Wilstrop, York

On Heathered Moor

On Heathered Moor

  • 6 guests

  • 3 bedrooms

Helmsley, York

Holly & Stone

Holly & Stone

  • 6 guests

  • 3 bedrooms

Pickering, North Yorkshire

Cottage on the Hill

Cottage on the Hill

  • 4 guests

  • 2 bedrooms

Coneysthorpe, York

Peace On The Horizon

Peace On The Horizon

  • 6 guests

  • 3 bedrooms

Runswick Bay, Saltburn-by-the-Sea

As You Wish

As You Wish

  • 2 guests

  • 1 bedrooms

Whitby, North Yorkshire

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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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