Popular Features
Sleeps
Sleeps
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Popular Cottages
- Woodland View
- Waterside Lodge One
- The Mill Loft Gilling West
- Coldmoor Lodge 6
- Keepers Hide at Wuthering Huts
- Field Barn Hut
- Tack Room Cottage
- Edmunds Cottage
- The Culverhouse
- Margaret’s in Driffield
- Old Station Farm
- The Dove Cote
- Station House
- Heathcliff
- West End Lodge in Ulrome
- The Malt Kiln
- Roseberry Lodge 3
- Ingleborough
- Fox's Den
- Bell Cottage
- Mere Walk in Hornsea
- Wellhead Cottage in Haworth
- The Old Station House
- Boavista
- Lovesome Cottage
- St Hilda's Lodge
- Loft Cottage
- The Orchid
- Moorgate Lodge at Moorgate Farm
- Joes Barn
Helmsley Holiday Cottages
Our curated collection of Helmsley cottages has something for everyone... Whether you're idea of a great holiday is a modern glamping pod, or a rustic thatched cottage that's a hundred years old, we've got you covered! Each of our rentals features a private hot tub and everything you need for your next family holiday, romantic retreat or that getaway with a group of friends. Discover find your perfect Helmsley holiday home today.
Visitor Rating
5
- Private wood-fired hot tub
- Panoramic North York Moors views
- Working farm setting experience
- Award-winning luxury glamping lodge
- Easy access to Helmsley attractions
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Visitor Rating
4.3
- Private hot tub with country views
- Studio on peaceful working farm
- North York Moors National Park location
- Walking trails from your doorstep
- Welcome pack and essentials included
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Visitor Rating
4.8
- Private hot tub in enclosed garden
- Sleeps 6 with 3 en-suites
- Two dogs welcome with private field
- Tennis court and billiards room access
- Wood burner in 30ft living area
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Visitor Rating
5
- Wood-fired hot tub with views
- Off-grid eco-friendly power systems
- Historic 1707 cottage features
- Direct moorland walking access
- Pet-friendly working farm location
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Visitor Rating
5
- Private hot tub summerhouse
- Cosy woodburner atmosphere
- Award winning luxury cottage
- Pet friendly enclosed garden
- North Yorkshire Moors access
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Visitor Rating
5
- Private hot tub for two
- Handcrafted shepherd's hut design
- Adults only romantic retreat
- Dog friendly accommodation
- North Yorkshire Moors location
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Visitor Rating
5
- Private hot tub with views
- Wood burning stove included
- Three bedrooms sleep five
- Two dogs welcome free
- Doorstep walking routes available
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Visitor Rating
4.8
- Georgian house sleeping 15 guests
- Hot tub in private courtyard
- Six bedrooms with four-poster beds
- Three miles from Malton town
- Parking for five cars
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- Private hot tub for six
- Romantic barn conversion setting
- Walking trails from doorstep
- Twenty-five minutes to York
- Pet-friendly with secure garden
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Visitor Rating
5
- Private hot tub for five
- Working farm with sheep
- No light pollution stargazing
- Direct cycle route access
- Homemade welcome pack included
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Visitor Rating
4.7
- Private hot tub for four
- Boutique luxury interior design
- Castle Howard two miles away
- Enclosed garden with BBQ
- Village pub directly opposite
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- Private hot tub with countryside views
- Three bedrooms sleeping six guests
- PlayStation 4 and Smart TVs throughout
- Dedicated dog-walking field for three pets
- Near Flamingo Land and moorland trails
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Visitor Rating
5
- Stunning countryside views
- Luxury hot tub
- Two en-suite bedrooms
- Spotlessly clean
- Electric vehicle charging
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Visitor Rating
4.2
- Private hot tub included
- Studio layout sleeps two
- Pet friendly accommodation
- Underfloor heating throughout
- Enclosed garden with furniture
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- Private hot tub for four
- Contemporary single storey design
- Woodburner for cosy evenings
- York Golf Club on doorstep
- Seven miles from historic York
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Visitor Rating
5
- Private hot tub for 4
- Accessible single storey design
- Dog friendly no charge
- Contemporary 2021 build
- York 7 miles away
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Visitor Rating
5
- Private hot tub for five
- Ground floor contemporary design
- Seven miles from York centre
- Private parking three cars
- Woodburner with initial logs
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Visitor Rating
5
- Private hot tub for six
- Award-winning cottage quality
- York just seven miles away
- Woodburner and sound system
- Golf course on doorstep
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Visitor Rating
4.4
- Hot tub on sun deck
- Traditional stone-built cottage
- Sleeps five across two bedrooms
- Village location near Pickering
- Split-level garden with patio
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Visitor Rating
4.9
- Private hot tub on enclosed decking
- Excellent on-site pub with great food
- Edge of North York Moors location
- Modern, clean single-storey accommodation
- King-size bed with quality linens
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Visitor Rating
4.9
- Private hot tub
- Genuine log cabin feel
- Excellent pub 0.1 miles away
- Two king-size bedrooms
- Beautiful rural Yorkshire location
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Visitor Rating
4.7
- Private hot tub on decking
- Two king-size bedrooms with TVs
- Immaculately clean throughout
- On-site pub with Thai food
- Perfect North York Moors location
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Visitor Rating
5
- Private hot tub with countryside views
- Two king-size bedrooms with en-suites
- Excellent Thai food next door
- Spotlessly clean luxury lodge
- Gated park with safe grounds
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Visitor Rating
4.8
- Private hot tub
- Next door to excellent pub
- King-size bedroom with Smart TV
- Edge of North York Moors
- Modern kitchen with all appliances
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Visitor Rating
4.9
- Private hot tub on enclosed deck
- Excellent Thai food at local pub
- Edge of North York Moors
- King-size bed with luxury bathroom
- Peaceful countryside location
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Visitor Rating
4.9
- Private hot tub
- Stunning countryside views
- 9-acre dog walking field
- Super-king bed
- Underfloor heating throughout
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Visitor Rating
4.9
- Private hot tub with stunning views
- Secure 9-acre dog walking field
- Total seclusion and privacy
- Luxury interior with underfloor heating
- Spectacular North York Moors location
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Visitor Rating
4.9
- Private hot tub with stunning views
- Dog-friendly with 9-acre exercise field
- Modern open-plan living space
- Perfect location for moors and coast
- King-size bed for ultimate comfort
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Visitor Rating
4.6
- Private hot tub
- Stunning countryside views
- Dog-friendly (3 dogs welcome)
- Traditional wood burner
- Peaceful North Yorkshire location
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Visitor Rating
4.7
- Private hot tub
- Games room with pool table
- Dog-friendly with enclosed garden
- Two king-size bedrooms
- Countryside location near Stokesley
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Explore more of Yorkshire
Popular towns and villages in and around Helmsley
Addingham Arncliffe Askrigg Aysgarth Bagby Bainbridge Bedale Bempton Beverley Bishop Monkton Bishop Wilton Brandesburton Bridlington Brierley Burlington Burnsall Carlton Catterick Cayton Cononley Cottingham Coxwold Denholme Doncaster Driffield Dunford Bridge Easingwold East Ayton Filey Flamborough Folkton Giggleswick Glaisdale Grassington Great Ayton Guisborough Harewood Harrogate Haworth Hellifield Helmsley Heptonstall Hetton Hinderwell Holmfirth Hopton Hornby Hornsea Hovingham Huddersfield Hunmanby Ilkley Ingleton Keighley Kirby Hill Kirkbymoorside Knaresborough Knayton Lealholm Leeds Leyburn Lofthouse Long Preston Lothersdale Malham Malton Marsden Masham Mickleton Middleton Mulgrave Muston Mytholmroyd Nawton Norton Nunnington Oakworth Otley Oxenhope Pateley Bridge Pickering Pocklington Ravenscar Rawdon Redcar Reeth Richmond Ripon Ripponden Robin Hood's Bay Romaldkirk Runswick Bay Saltaire Sandsend Scarborough Seamer Sedbergh Selby Settle Shepley Sheriff Hutton Silsden Skipsea Skipton Sleights Slingsby Sowerby Sowerby Bridge Staithes Stanley Stokesley Sutton Thornhill Threshfield Todmorden Ugthorpe Wakefield Walkington Wentworth West Tanfield Wetherby Whitby Withernsea Wyke York