Book Luxury Monthly Rentals in Helmsley

We selected the 1008 homes worth renting in this location

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Home spotlights in Helmsley

Whispering Pines Cottage

Whispering Pines Cottage

  • 4 guests

  • 2 bedrooms

Old Byland, York

Located in the scenic village of Old Byland, Drey Cottage is a beautiful holiday home with plenty of charm. This dog friendly property provides a peaceful retreat for couples, families and small groups of friends, accommodating up to four guests.

Old Byland Hideaway

Old Byland Hideaway

  • 2 guests

  • 1 bedrooms

Old Byland, York

Old Byland Hideaway is a charming and cosy cottage nestled in the picturesque village of Old Byland in North Yorkshire. Just a short distance from the market town of Helmsley, this one-bedroom holiday home offers a perfect retreat for couples seeking tranquility and relaxation.

The Seashell

The Seashell

  • 6 guests

  • 3 bedrooms

Whitby, North Yorkshire

This seaside home is perfectly positioned in the heart of Whitby for exploring its bustling town centre and sandy shores. Bright and stylish, the apartment makes great use of space, with an open concept design that is perfect for kicking up your feet and unwinding after an exciting day out.

Beach Blues

Beach Blues

  • 2 guests

  • 1 bedrooms

Saltburn-by-the-Sea, Redcar and Cleveland

The Victorian spa town of Saltburn-by-the-Sea makes for an excellent seaside escape. It’s a real coastal retreat, surrounded by charming seaside towns and villages – you can use Saltburn as your base for exploring the area.


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

Explore the 1008 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

The Riverside Cottage

The Riverside Cottage

  • 4 guests

  • 2 bedrooms

Richmond, North Yorkshire

The Yorkshire Retreat

The Yorkshire Retreat

  • 12 guests

  • 6 bedrooms

Kepwick, Thirsk

Willow in Bloom

Willow in Bloom

  • 16 guests

  • 8 bedrooms

Rosedale East Side, North Yorkshire

Let's Walk By the River

Let's Walk By the River

  • 4 guests

  • 2 bedrooms

Hurworth-on-Tees, Darlington

Harbour Hopes

Harbour Hopes

  • 8 guests

  • 4 bedrooms

Whitby, North Yorkshire

Yorkshire Gem

Yorkshire Gem

  • 4 guests

  • 2 bedrooms

Kirkbymoorside, York

Cherry Tree

Cherry Tree

  • 4 guests

  • 4 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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