Rent Luxury Accommodation for Groups in Helmsley

We selected the 1066 homes worth renting in this location

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Home spotlights in Helmsley

Seashells by the Seashore

Seashells by the Seashore

  • 12 guests

  • 6 bedrooms

Whitby, North Yorkshire

Check into this handsome Whitby townhouse for seaside living at its most refined and stylish. Set across five floors united by elegant interiors, there’s room for all twelve of you to make yourselves at home here.

Blackberry Cobbler

Blackberry Cobbler

  • 4 guests

  • 2 bedrooms

Haworth, Keighley

This quaint stone-built terraced cottage on Haworth’s historic cobbled main street puts you within easy reach of the area’s local pubs, shops, cafes and restaurants, not to mention the Bronte Parsonage Museum less than a five-minute walk away. The decor is exactly what you’d expect of a cosy, rustic cottage – original beams and stonework, and a wood-burning stove in the downstairs living room.

The Edge of the Meadow

The Edge of the Meadow

  • 8 guests

  • 4 bedrooms

Wilstrop, York

This delightful family home boasts wonderful views of Gilling Gap from the first-floor bedrooms. The home was originally owned by a family of stonemasons who worked on local churches, houses and schools – there’s a real sense of history here.

On Heathered Moor

On Heathered Moor

  • 6 guests

  • 3 bedrooms

Helmsley, York

This pretty retreat is in the historic market town of Helmsley, sits on the edge of the North York Moors National Park. The 110 mile-long Cleveland Way National Trail begins in Helmsley and takes you through the heather-clad hills of the Moors to the cliffs and coast of Filey Brigg – a nine-day trek in total, but you can stop your car at any point along its length.


We selected the top 3% holiday homes in Helmsley Accommodation for Groups

Explore the 1066 most perfect homes in our collection

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Most popular homes in Helmsley

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

Old Byland Hideaway

Old Byland Hideaway

  • 2 guests

  • 1 bedrooms

Old Byland, York

Yorkshire Gem

Yorkshire Gem

  • 4 guests

  • 2 bedrooms

Kirkbymoorside, York

A Glimpse of Glory

A Glimpse of Glory

  • 5 guests

  • 3 bedrooms

Stockton-on-Tees, England

Pine Tree Chapel

Pine Tree Chapel

  • 6 guests

  • 2 bedrooms

Wilstrop, York

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Check upcoming rates & availability for Helmsley Accommodation for Groups


Frequently asked questions

Reserve a stay in one of the impeccable homes in our collection of luxury Group Holiday Accommodation in Helmsley. You won't find such consistent quality anywhere else, as every single Plum Guide home comes fully furnished with all linens, a brilliantly-equipped kitchen, and essential bathroom toiletries included. Our experts really do obsess over the smallest details, with shower pressure and a bedroom's decibel levels being tested to ensure absolute quality in your hunt for the perfect home. Rent Helmsley Accommodation for Groups today, and learn the true meaning of luxury. Call on our team of experts too, who can help you through the booking process and guarantee that you end up with the ultimate home for you.

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