Book Luxury Monthly Rentals in Helmsley

We selected the 1066 homes worth renting in this location

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Home spotlights in Helmsley

Pat-a-Cake

Pat-a-Cake

  • 2 guests

  • 1 bedrooms

Pickering, North Yorkshire

This elegant cottage in the ancient town of Pickering had us on the private outdoor terrace alone. But step inside, and this home keeps on surprising.

Romancing the Stone

Romancing the Stone

  • 5 guests

  • 3 bedrooms

Crayke, York

This charming home in the heart of Yorkshire is a real escape from reality. A traditional stone cottage in the village of Crayke, it’s got bags of character, plenty of style and next-level comfort.

Farmhand

Farmhand

  • 8 guests

  • 4 bedrooms

Ebberston, Scarborough

If you’re looking for an escape to the country, you couldn’t do much better than this charming farmhouse located amidst North Yorkshire’s beautiful rolling hills. Surrounded by a working farm, you'll feel transported to another world as you step into this beautifully detailed home.

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.


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

Explore the 1066 most perfect homes in our collection

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Most popular homes in Helmsley

Cherry Tree

Cherry Tree

  • 4 guests

  • 4 bedrooms

Helmsley, York

Yorkshire Homestead

Yorkshire Homestead

  • 16 guests

  • 8 bedrooms

East Heslerton, Malton

Osmund's Firewood

Osmund's Firewood

  • 8 guests

  • 4 bedrooms

Osmotherley, Northallerton

Yorkshire Enchantment

Yorkshire Enchantment

  • 14 guests

  • 7 bedrooms

Nether Silton, Thirsk

Seashells by the Seashore

Seashells by the Seashore

  • 12 guests

  • 6 bedrooms

Whitby, North Yorkshire

Blackberry Cobbler

Blackberry Cobbler

  • 4 guests

  • 2 bedrooms

Haworth, Keighley

The Edge of the Meadow

The Edge of the Meadow

  • 8 guests

  • 4 bedrooms

Wilstrop, York

On Heathered Moor

On Heathered Moor

  • 6 guests

  • 3 bedrooms

Helmsley, York

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Helmsley, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Helmsley Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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