Book Luxury Holiday Rentals in Helmsley

Award-winning homes from £98

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Home spotlights in Helmsley

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.

The Woodlark

The Woodlark

  • 6 guests

  • 3 bedrooms

Sutton-on-the-Forest, York

Nestled in Sutton-on-the-Forest, just 8 miles north of York, this charming 18th-century cottage welcomes you in with open arms. Perfect for families, the generous country kitchen will quickly become the place where everyone gathers, spilling out into the walled garden for alfresco dining in summer months.

Northern Orchid

Northern Orchid

  • 4 guests

  • 2 bedrooms

Saltburn-by-the-Sea, Redcar and Cleveland

This is a home steeped in history. Built in the early 1800s, it was a bank for over 100 years, before becoming an art gallery in the 2010s.

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 1098 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

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

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

The Fen Violet

The Fen Violet

  • 2 guests

  • 1 bedrooms

Lockton, Pickering

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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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