Book Luxury Holiday Rentals in Helmsley

Award-winning homes from £98

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Home spotlights in Helmsley

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.

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 Riverside Cottage

The Riverside Cottage

  • 4 guests

  • 2 bedrooms

Richmond, North Yorkshire

Shhh. Can you hear that sound?

Yorkshire Gem

Yorkshire Gem

  • 4 guests

  • 2 bedrooms

Kirkbymoorside, York

Dale End is a charming holiday home superbly situated in Kirkbymoorside, York, ideally for exploring the idyllic North York Moors National Park. Newly refurbished to the highest standard, this stylish and sleek two-bedroom property offers a homely atmosphere that exudes warmth.


We selected the top 3% holiday homes in Helmsley Holiday Rentals

Explore the 1036 most perfect homes in our collection

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Most popular homes in Helmsley

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

The Old Piggery

The Old Piggery

  • 2 guests

  • 1 bedrooms

Slingsby, York

The Edge of the Meadow

The Edge of the Meadow

  • 8 guests

  • 4 bedrooms

Wilstrop, York

Country Diaries

Country Diaries

  • 4 guests

  • 2 bedrooms

Stockton-on-Tees, England

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Helmsley. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Helmsley has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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