Cottages in Helmsley

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Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 141 cottages

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Map View
Exterior view of a row of brick and stone houses with windows and doors on a street at Howe End Cottage in Kirkbymoorside
21
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms3
  • PetsYes

    4.7

Cosy town house in heart of Kirkbymoorside. Three storeys, welcoming accommodation. Convenient location, good base for moors, coast, York and more. (Ref. 17787)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £653

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A row of brick and stone houses with tiled roofs and multiple doors and windows along a roadside at Duckys in Pickering
35
Pickering, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms3
  • PetsYes

    4.8

    Sykes Rating

A lovely three-bedroom terraced cottage resting in Pickering, North Yorkshire. Pet-friendly. Near a National Park. Off-road parking. Woodburning stove. Kirkbymoorside 6.7 miles; Helmsley 12.2 miles; Scarborough 18.4 miles. (Ref. 1102719)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £456

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Front of a stone house with a wooden gate and fence with several potted plants on the ground at Stone Cross in Spaunton near Hutton-Le-Hole
15
Spaunton near Hutton-Le-Hole, North York Moors National Park, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Sykes Rating

Beautiful stone cottage in the North York Moors National Park, close to the village of Hutton-le-Hole. Exposed beams. Surrounded by countryside. Hutton-le-Hole 1.5 miles. (Ref. 975266)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from £343

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A stone exterior wall with multiple doors and windows a chair and table on the patio with flower pots at The Byre in Thirsk
29
Thirsk, North York Moors National Park, YO7
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Sykes Rating

A stone-built cottage resting on the outskirts of Thirsk. Ground-floor accommodation. WiFi. Pets welcome. York 27 miles; Harrogate 30 miles. (Ref. 1002964)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £333

Last booked yesterday
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A small stone cottage with a green door and window surrounded by paved ground and a garden at Peg's Cottage in Pockley near Helmsley
16
Pockley near Helmsley, North York Moors National Park, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Sykes Rating

Pretty, detached, ground floor stone cottage in a small hamlet near Helmsley. Cosy, characterful accommodation for couples. WiFi. Pretty garden. Superb walking country. Helmsley 2 miles. (Ref. 917006)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine

7 nights from £330

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Stone cottage facade with three doors and multiple windows on the front at Crooked Cottage in Kirkbymoorside
24
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

A charming, Grade II listed cottage on the edge of pretty Kirkbymoorside, Yorkshire. Pickering 6 miles. Close to North York Moors National Park. (Ref. 985142)

  • Wi-fi
  • Washing machine

7 nights from £395

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Exterior view of a two-story brick house with white framed windows and doors surrounded by a garden at Sunnyside Garden Cottage in Husthwaite
11
Husthwaite, North Yorkshire, YO61
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Sykes Rating

A spacious annexe cottage in the village of Hushtwaite in North Yorkshire. Open-plan living. En-suite. York 13 miles. (Ref. 959719)

  • Wi-fi
  • Off-road parking
  • Games room

7 nights from £312

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An outdoor area with a brick building, table and chairs at Stable Cottage in Cawton near Hovingham
19
Cawton near Hovingham, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Sykes Rating

Detached pet-friendly cottage near Hovingham. Single-storey cottage, rural position on arable farm estate, underfloor heating. Well equipped and comfortable. Close to Nunnington, Castle Howard, pretty market towns. Hovingham 3 miles. (Ref. 21723)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £304

Last booked 2 days ago
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A stone building with two green doors and a bench next to a pond with lily pads at The Cottage in Thirsk
25
Thirsk, North York Moors National Park, YO7
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Sykes Rating

A stone-built cottage which rests on the outskirts of Thirsk, North Yorkshire. Open-plan. WiFi. Just a moment’s walk from the Cleveland National Trail. York 27 miles. (Ref. 1004365)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £296

Last booked yesterday
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Exterior of a brick cottage with a tiled roof small windows flower pots and a black metal gate at Chestnut Cottage in Kirkbymoorside
14
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Sykes Rating

A well-presented barn conversion, on a working farm and close to the Yorkshire town of Kirkbymoorside. Open-plan living. En-suite. Near North York Moors National Park. Pet-friendly. (Ref. 974386)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine

7 nights from £320

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A stone cottage with blue window frames and a wooden picnic table in a gravel courtyard at Foxglove Cottage in Harome
11
Harome, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.2

    Sykes Rating

A snug ground-floor cottage tucked away in the quiet village of Harome near Beadlam in North Yorkshire. Electric fire. Romantic retreat. Helmsley 2.7 miles; Pickering 12.3 miles; York 22.5 miles. (Ref. 1069744)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £608

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A stone cottage with a tiled roof surrounded by bushes and flowers with a wooden door and two windows at Rose Cottage in Kirkbymoorside
18
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Sykes Rating

A characterful barn conversion resting on a working farm near the town of Kirkbymoorside. TV with Freeview. Countryside views. Near North York Moors National Park. Dog-friendly. (Ref. 974385)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom

7 nights from £320

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A small patio garden with a round table, two chairs, potted plants, and a wooden fence at The Old Forge in Stillington
31
Stillington, North Yorkshire, YO61
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Sykes Rating

Pretty little detached cottage in Stillington village, midway between York and Helmsley. All ground floor with comfortable open plan living. Perfect romantic retreat. York 11 miles. (Ref. 30893)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £429

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A living area with a sofa and coffee table adjacent to a kitchen with white cabinets and a wooden door at Crumble's Hideaway in Kirkbymoorside
14
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

This delightful cottage resides in Kirkbymoorside, North Yorkshire. Close to amenities. Couples’ getaway. En-suite bathroom. Smart TV. Pickering 7.7 miles; Helmsley 5.6 miles. (Ref. 963205)

  • Wi-fi

7 nights from £388

Last booked yesterday
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A cabin with large windows and a wooden deck surrounded by trees at Cropton Golden Oak Cropton Forest
20

Holiday Park

Cropton Forest, North York Moors National Park, YO18
  • Sleeps2
  • Bedrooms1
  • PetsYes

Forest Holidays Golden Oak cabin is one of 58 cabins found within a woodland meadow of Cropton Forest in the North York Moors National Park. (Ref. 1146556)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher

7 nights from £1020

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A row of brick houses with arched windows and doors with potted plants outside at Chapel Cottage in Stillington near Easingwold and York
33
Stillington near Easingwold and York, North Yorkshire, YO61
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.8

    Sykes Rating

Attractive, period cottage in pretty Stillington village. Character beams, open fire, enclosed sunny courtyard garden. Quality accommodation, well-equipped and comfortable. Many attractions close by. York 10 miles. (Ref. 28836)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from £439

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A wooden cabin with a porch, two chairs, a small table, and a grassy lawn at Rising Sun in Kirkbymoorside
22
Kirkbymoorside, North York Moors National Park, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A lovely one-bedroom lodge perched near Kirkbymoorside, North Yorkshire. Pet-free. Wood fired hot tub. Near National Park. Romantic. Pickering 5.8 miles; Helmsley 7.3 miles. (Ref. 1049218)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Washing machine

7 nights from £497

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An outdoor seating area with a table and two chairs next to a small shed and a covered seating area at Bellwether in Helmsley
24
Helmsley, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A superb, shepherd’s hut situated on the outskirts of the market town of Helmsley. Woodburner. WiFi. Rural views. Kirkbymoorside 3.9 miles; Pickering 10.9 miles. (Ref. 986040)

  • Wi-fi
  • Ground floor bedroom

7 nights from £305

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A wooden cabin with a porch and outdoor seating area with a small table and chairs at Peep o Day in Kirkbymoorside
22
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A beautiful one-bedroom lodge resting on the outskirts of Kirkbymoorside, North Yorkshire. Off-road parking. Near a National Park. Romantic. Pickering 5.8 miles; Helmsley 7.3 miles. (Ref. 1049219)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Washing machine

7 nights from £497

Last booked 2 days ago
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A stone cottage with red tile roof and white framed windows next to a small gravel area with a wooden fence and surrounded by greenery at Yon Cottage in Stonegrave near Hovingham
22
Stonegrave near Hovingham, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A wonderful, semi-detached cottage settled in Stonegrave near Hovingham, North Yorkshire. Woodburning stove. Near National Park. Romantic. Helmsley 5.9 miles; Malton 10.1 miles; York 18.5 miles. (Ref. 1106690)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £350

Last booked 8 hours ago
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Map View

On the border of the North York Moors National Park, this delightful market town is a haven for walkers and lovers of the outdoors.

Why Helmsley?

After an action-packed day among the wonders of the North York Moors, our Helmsley cottages enjoy close proximity to the town's charming pubs and delightful tea rooms to recharge the batteries. There is a selection of excellent independent shops and a weekly market along its attractive streets to pick up some of the finest local produce. From your Helmsley accommodation, be sure to explore the stunning Helmsley Castle and sculpture garden, as well as Duncombe Park and the National Centre for Birds of Prey for nature enthusiasts.

Places to Visit near Helmsley

Our range of cottages in Helmsley rest on the southern fringes of the North York Moors National Park, perfectly based for a break filled with activity and adventure. This National Park hugging the coast of Yorkshire has much to offer, not least its wide range of walks and cycle paths taking in some of the finest landscape scenery imaginable. Discover a handful of unique villages in and around the spectacular moors, waiting to be explored with rustic inns and delightful cafés offering those mid-adventure refreshments. Make your Helmsley cottage holiday a memorable one by visiting popular spots such as Ampleforth, Hutton-le-Hole, Kirkbymoorside, Pickering, Ripon and Thirsk.

Types of Holidays

All types of holidays can be enjoyed across Yorkshire with Sykes, whether you're seeking a Yorkshire cottage by the sea, or more of a rural retreat at a cottage in the Yorkshire countryside. Bring your dog along to enjoy the sublime walking country nearby by booking a North York Moors pet-friendly cottage, or really treat yourselves to a break in a Yorkshire luxury cottage.