Book Family Friendly Rentals in Helmsley

We selected the 894 homes worth renting in this location

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Home spotlights in Helmsley

Unbridled

Unbridled

  • 10 guests

  • 5 bedrooms

Ripon, North Yorkshire

A luxurious, modern conversion, these former stables and coach house once belonged to the nearby manor. Set in extensive grounds but with its own garden, this is one magnificent place to stay in North Yorkshire.

Tranquil Teeside Cottage

Tranquil Teeside Cottage

  • 4 guests

  • 2 bedrooms

Barnard Castle, England

Whether you're traveling with friends or family, Tranquil Teeside Cottage will be your tranquil home away from home as soon as you step through the door. Sleeping up to four guests, this charming cottage boasts an inviting open plan living, kitchen and dining room that exudes countryside charm.

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 894 most perfect homes in our collection

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Most popular homes in Helmsley

Yorkshire Homestead

Yorkshire Homestead

  • 16 guests

  • 8 bedrooms

East Heslerton, Malton

Holly & Stone

Holly & Stone

  • 6 guests

  • 3 bedrooms

Pickering, North Yorkshire

Lost in Thought

Lost in Thought

  • 6 guests

  • 3 bedrooms

Pickering, North Yorkshire

The Salt Collector

The Salt Collector

  • 2 guests

  • 1 bedrooms

West Cliff, Whitby

Pine Tree Chapel

Pine Tree Chapel

  • 6 guests

  • 2 bedrooms

Wilstrop, York

The Old Piggery

The Old Piggery

  • 2 guests

  • 1 bedrooms

Slingsby, York

No Warmer Welcome

No Warmer Welcome

  • 24 guests

  • 11 bedrooms

Brotton, Saltburn-by-the-Sea

Heathcliff, It's Me

Heathcliff, It's Me

  • 4 guests

  • 2 bedrooms

Guisborough, England

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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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