Book Family Friendly Rentals in Helmsley

We selected the 944 homes worth renting in this location

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Age 1 to 12

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Home spotlights in Helmsley

The Daffodil Garden

The Daffodil Garden

  • 2 guests

  • 1 bedrooms

Scargill, Barnard Castle

This charming Tudor castle, built in 1560, has been fully restored to create the perfect romantic retreat for two. Set in the picturesque Teesdale landscape, this historic property is located near the Yorkshire Dales and Lake District National Park, as well as the North Pennines Area of Outstanding Natural Beauty.

Rural Heart

Rural Heart

  • 6 guests

  • 3 bedrooms

Appleton East and West, North Yorkshire

This cosy home provides a true countryside escape. It's located on the cusp of Wensleydale and resides near the stretching natural beauty of the Yorkshire Dales.

Here's A Dream

Here's A Dream

  • 2 guests

  • 1 bedrooms

Wilstrop, York

Formerly a stonemason's workshop, who worked on local churches, schools and Ampleforth Abbey, this home has now been fully renovated for a comfortable stay. There's a wood burner in the double-height living room for cosy evenings in and a small courtyard for taking in the Yorkshire air.

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.


We selected the top 3% holiday homes in Helmsley Family Friendly Rentals

Explore the 944 most perfect homes in our collection

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Most popular homes in Helmsley

Lost in Thought

Lost in Thought

  • 6 guests

  • 3 bedrooms

Pickering, North Yorkshire

Holly & Stone

Holly & Stone

  • 6 guests

  • 3 bedrooms

Pickering, North Yorkshire

Tranquil Teeside Cottage

Tranquil Teeside Cottage

  • 4 guests

  • 2 bedrooms

Barnard Castle, England

Enchanted Forest

Enchanted Forest

  • 14 guests

  • 7 bedrooms

Darlington, England

Tranquil Farmhouse

Tranquil Farmhouse

  • 6 guests

  • 3 bedrooms

Old Byland, York

The Old Piggery

The Old Piggery

  • 2 guests

  • 1 bedrooms

Slingsby, York

Cozy Rose Retreat

Cozy Rose Retreat

  • 4 guests

  • 2 bedrooms

Pickering, North Yorkshire

The Fen Violet

The Fen Violet

  • 2 guests

  • 1 bedrooms

Lockton, Pickering

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Check upcoming rates & availability for Helmsley Family Friendly Rentals


Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Helmsley. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Helmsley Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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