Luxury Long Stay Rentals in Helmsley

We selected the 1036 homes worth renting in this location

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Home spotlights in Helmsley

On The Market

On The Market

  • 4 guests

  • 2 bedrooms

Helmsley, York

Helmsley is a town drenched in unique attractions. A vibrant market selling chic items sits nearby to Michelin-star restaurants, showcasing the town's diversity.

Sweet Beams

Sweet Beams

  • 4 guests

  • 2 bedrooms

Brotton, Saltburn-by-the-Sea

If you’d like a peaceful stay in the Yorkshire countryside, while still being within easy reach of the fun-filled Yorkshire coast, this home offers the perfect sanctuary. Located in the little village of Brotton, just a short drive from Saltburn-by-the-Sea, this characterful cottage has loads of traditional features that make it feel homely and quaint, such as the exposed beam ceilings, ornate wooden furniture and chintzy soft furnishings.

Willow in Bloom

Willow in Bloom

  • 16 guests

  • 8 bedrooms

Rosedale East Side, North Yorkshire

Perched above the tiny village of Rosedale Abbey, this former vicarage has beautiful views of the rolling Yorkshire countryside. There’s a local shop, tea room, pub and café within walking distance, but it’s all about rambles into the countryside here.

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 Long Stay Rentals

Explore the 1036 most perfect homes in our collection

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Most popular homes in Helmsley

Charming Norton Hideaway

Charming Norton Hideaway

  • 4 guests

  • 2 bedrooms

Norton, Stockton-on-Tees

Tranquil Teeside Cottage

Tranquil Teeside Cottage

  • 4 guests

  • 2 bedrooms

Barnard Castle, England

Yorkshire Gem

Yorkshire Gem

  • 4 guests

  • 2 bedrooms

Kirkbymoorside, York

On Heathered Moor

On Heathered Moor

  • 6 guests

  • 3 bedrooms

Helmsley, York

Pine Tree Chapel

Pine Tree Chapel

  • 6 guests

  • 2 bedrooms

Wilstrop, York

The Yorkshire Retreat

The Yorkshire Retreat

  • 12 guests

  • 6 bedrooms

Kepwick, Thirsk

Sea Of Wonders

Sea Of Wonders

  • 6 guests

  • 3 bedrooms

Whitby, North Yorkshire

Boats in the Harbour

Boats in the Harbour

  • 9 guests

  • 4 bedrooms

Whitby, North Yorkshire

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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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