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- The Brew House
- Damson Barn
- Ashen Glade Lodge
- St Hilda's Lodge
- Tannery Cottage
- Broom Barn
- Partridge Place
- Swan At Grace View
- 3 Glendowne Terrace
- Well Cottage
- Flittermouse Barn
- Willow House
- The Mill Farmhouse Gilling West
- The Power House
- Low Pasture Cottage
- Meadow View
- Otters Holt
- The Hay Barn
- Duckling Lodge
- Cliff House
- Green Barn
- Apple Barn
- Swaswara
- Skylark The Woodlands Collection
- Coppa Hill Barn
- Barn Owl
- Owl's Hoot
- Churra
- Lapwing
- St Edmunds House
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
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
4.9
- Hot tub available on request
- 7ft super king-size bed
- Edge of North York Moors
- Dog friendly 2 dogs
- Wood burner and private terrace
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- Private hot tub with stargazing
- Two en-suite bedrooms
- Single-floor barn conversion
- Wood burner and Smart TV
- EV charging on site
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Visitor Rating
4.9
- Private hot tub in suntrap garden
- Luxury barn conversion sleeps 4
- Games room sauna and mini gym
- Pet friendly with secure garden
- Minutes from Helmsley and York
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- Private hot tub in secluded garden
- Grade II Listed Yorkshire cottage
- Two king-size bedrooms sleeps 4
- Wood burner and 75" Smart TV
- Dog friendly with enclosed garden
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Visitor Rating
4.5
- Private hot tub in rear garden
- Grade II Listed renovated cottage
- King-size bed with wooden floors
- Walks from the village door
- One dog welcome
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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 with countryside views
- Two en-suite bedrooms sleep four
- Working farm with doorstep walks
- Near Flamingo Land and Castle Howard
- Pet-friendly welcomes two dogs
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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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- Private hot tub on decking
- Dog-friendly with 20-acre field
- 2 miles from Moors Railway
- PS4 and Smart TVs throughout
- Both bedrooms have en-suites
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- Canopy-covered hot tub in garden
- Scandi log cabin on 60-acre estate
- Dalby Forest 5 miles away
- Pickering heritage railway 1.5 miles
- PlayStation 4 and Hypnos mattresses
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- Private covered hot tub
- Dog friendly up to 3 dogs
- Both bedrooms en-suite
- 60-acre estate with dog field
- 5 miles from Flamingo Land
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- Private hot tub included
- 20-acre on-site dog field
- 3 en-suite boutique bedrooms
- 1.5 miles from Pickering
- Enclosed garden with BBQ
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- Private hot tub on full-width decking
- Up to three dogs welcome
- 60-acre estate with dog-walking field
- Both bedrooms fully en-suite
- Under 5 miles from Flamingo Land
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- Private hot tub included
- North York Moors location
- Minutes from Pickering town
- Near Whitby and Scarborough
- Dalby Forest 8 miles away
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- Private hot tub on decking
- 3 dogs welcome on-site
- 20-acre dog walking field
- 1 mile from Pickering
- Dalby Forest 5 miles away
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- Private hot tub in enclosed garden
- Wood burner and plush sofas
- 1 mile from steam railway
- Up to 3 dogs welcome
- Vale of Pickering views
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- Private covered hot tub on decking
- Dog friendly, up to 3 dogs
- 60-acre woodland estate setting
- Flamingo Land 5 miles away
- Pickering market town under 1 mile
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- Private hot tub on enclosed decking
- Sleeps 4 with 2 bathrooms
- Up to 3 dogs welcome
- Flamingo Land 5.5 miles away
- North Yorkshire Moors on the doorstep
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- Private hot tub under canopy
- Up to three dogs welcome
- Hypnos beds in both rooms
- 60-acre woodland site
- 1 mile from Pickering
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- Hot tub on private decking
- Next to woodland on 60-acre estate
- Dogs welcome up to three
- 1 mile from Pickering town
- 5 miles from Flamingo Land
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Visitor Rating
4.9
- 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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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
4.8
- 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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Explore more of Yorkshire
Popular towns and villages in and around Helmsley
Addingham Arncliffe Askrigg Aysgarth Bagby Bainbridge Bedale Beverley Bishop Monkton Brandesburton Bridlington Brierley Burlington Burnsall Carlton Catterick Cayton Cononley Cottingham Coxwold Doncaster Driffield Easingwold East Ayton Filey Folkton Giggleswick Glaisdale Grassington Great Ayton Guisborough Harewood Harrogate Haworth Hellifield Helmsley Hetton Hinderwell Hornby Hornsea Hovingham Hunmanby Ilkley Ingleton Keighley Kirby Hill Kirkbymoorside Knaresborough Knayton Lealholm Leeds Leyburn Lofthouse Long Preston Lothersdale Malham Malton Marsden Masham Mickleton Mulgrave Muston Nawton Norton Nunnington Oakworth Otley Oxenhope Pateley Bridge Pickering Pocklington Ravenscar Rawdon Redcar Reeth Richmond Ripon Robin Hood's Bay Romaldkirk Runswick Bay Sandsend Scarborough Seamer Sedbergh Settle Sheriff Hutton Silsden Skipsea Skipton Sleights Slingsby Sowerby Staithes Stokesley Sutton Threshfield Todmorden Ugthorpe Walkington Wentworth West Tanfield Whitby Withernsea