Book Luxury Holiday Rentals in Pickering

Award-winning homes from £98

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Home spotlights in Pickering

Yorkshire Homestead

Yorkshire Homestead

  • 16 guests

  • 8 bedrooms

East Heslerton, Malton

Set in one of the most beautiful parts of Yorkshire, this formerly derelict barn was chanced across by its owners in 2015, and lovingly converted into the stunning home it is today. The vibe is English country, with real moments of grandeur.

Sea Moss

Sea Moss

  • 6 guests

  • 3 bedrooms

Scalby, Scarborough

Make the great escape to this charming coastal lodge set in the postcard-pretty village of Scalby, fringing the archetypal seaside resort of Scarborough. Elegantly styled throughout, there's no need to tussle for the best room here.

Country Diaries

Country Diaries

  • 4 guests

  • 2 bedrooms

Stockton-on-Tees, England

Slow down and start living the country life at this newly-built cottage set deep in rural North Yorkshire on a private gated estate. Surrounded by green paddocks and grazing horses, its setting is postcard-perfect, and things only get better inside.

Cobbles of the Church Yard

Cobbles of the Church Yard

  • 4 guests

  • 2 bedrooms

Pickering, North Yorkshire

Housed in an old school house, the former residence of the head teacher at the local church school – this home retains much of its original character, while modern home luxuries spruce the space up with a contemporary twist. The interiors of the home present countryside chic with the addition of playful pops of colour in every room.


We selected the top 3% holiday homes in Pickering Holiday Rentals

Explore the 1040 most perfect homes in our collection

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Most popular homes in Pickering

Holly & Stone

Holly & Stone

  • 6 guests

  • 3 bedrooms

Pickering, North Yorkshire

Willow in Bloom

Willow in Bloom

  • 16 guests

  • 8 bedrooms

Rosedale East Side, North Yorkshire

Painter's Vista

Painter's Vista

  • 4 guests

  • 2 bedrooms

Thornton Dale, Pickering

Vintage Beauty

Vintage Beauty

  • 4 guests

  • 2 bedrooms

Saltburn-by-the-Sea, Redcar and Cleveland

Enchanted Forest

Enchanted Forest

  • 14 guests

  • 7 bedrooms

Darlington, England

Potter Hill Haven

Potter Hill Haven

  • 6 guests

  • 3 bedrooms

Pickering, North Yorkshire

Lost in Thought

Lost in Thought

  • 6 guests

  • 3 bedrooms

Pickering, North Yorkshire

Lister & Walker

Lister & Walker

  • 4 guests

  • 2 bedrooms

Whitby, North Yorkshire

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Pickering, North Yorkshire, England, United Kingdom. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Pickering, North Yorkshire, England, United Kingdom has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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