Helmsley is a beautiful old market town and its market cross serves as the starting point of the Cleveland Way, a 108 mile trek around the North Yorkshire Moors. As such, it has plenty of amenities for the visitor. Shopping is very good in Helmsley and it also has several quality inns and pubs to cater to the visiting walkers.

Helmsley is far more than just a way station - there are several places to visit making it a good place to stay for a few days. Helmsley Castle, built in the 1200s is a great place to start. The ruins of the castle loom over the town. The castle was intact until the Civil War when it was destroyed by the Parliamentarians. The fantastic Baroque home of the Duncombe family is also worth a visit. Duncombe Park offers centuries-old treasures to view, beautiful ornamental gardens and attractions for younger visitors. These two sights are within view from Helmsley Walled Garden but do not detract from the garden itself. This five-acre site, first built in 1756, is a fully functioning kitchen garden.

Helmsley has lovely old pubs, traditional tea houses and wonderful relaxing walks by the river. In short, it is an ideal place for a short break or for a longer getaway.

Cottage distance (in Miles)
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There are 35 cottages near Helmsley.

Lavender Cottage

4 star rating

Helmsley, North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 0
  • Distance from Helmsley (miles): 0

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Price from

£395-£789

4 star rating
Helmsley, North York Moors

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Price from

£395-£789

Sleeps: 4 Bedrooms: 2 Bathrooms: 1 Pets: 0

Pear Tree Cottage

4 star rating

Kirkbymoorside, North York Moors

  • Sleeps: 2
  • Bedrooms: 1
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 4

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Price from

£293-£530

4 star rating
Kirkbymoorside, North York Moors

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Price from

£293-£530

Sleeps: 2 Bedrooms: 1 Bathrooms: 1 Pets: 1

Ryecroft

4 star rating

Nunnington near Helmsley, North York Moors

  • Sleeps: 6
  • Bedrooms: 3
  • Bathrooms: 2
  • Number of Pets: 0
  • Distance from Helmsley (miles): 4

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Price from

£485-£1015

4 star rating
Nunnington near Helmsley, North York Moors

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Price from

£485-£1015

Sleeps: 6 Bedrooms: 3 Bathrooms: 2 Pets: 0

Plum Tree Cottage

4 star rating

Kirkbymoorside, North York Moors

  • Sleeps: 2
  • Bedrooms: 1
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 4

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Price from

£309-£600

4 star rating
Kirkbymoorside, North York Moors

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Price from

£309-£600

Sleeps: 2 Bedrooms: 1 Bathrooms: 1 Pets: 1

Sproxton Hall Cottages - Kirkdale Cottage

0 star rating

Sproxton, near Helmsley, North York Moors

  • Sleeps: 5
  • Bedrooms: 3
  • Bathrooms: 1
  • Number of Pets: 3
  • Distance from Helmsley (miles): 1

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Price from

£395-£979

0 star rating
Sproxton, near Helmsley, North York Moors

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Price from

£395-£979

Sleeps: 5 Bedrooms: 3 Bathrooms: 1 Pets: 3

Clematis Cottage

4 star rating

Helmsley, North York Moors

  • Sleeps: 3
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 0
  • Distance from Helmsley (miles): 0

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Price from

£333-£630

4 star rating
Helmsley, North York Moors

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Price from

£333-£630

Sleeps: 3 Bedrooms: 2 Bathrooms: 1 Pets: 0

Manor Cottage

4 star rating

Old Byland, near Helmsley, North York Moors

  • Sleeps: 8
  • Bedrooms: 4
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 4

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Price from

£325-£1035

4 star rating
Old Byland, near Helmsley, North York Moors

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Price from

£325-£1035

Sleeps: 8 Bedrooms: 4 Bathrooms: 1 Pets: 1

Finch Lodge

3 star rating

Nawton, near Helmsley, North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 2

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Price from

£249-£635

3 star rating
Nawton, near Helmsley, North York Moors

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Price from

£249-£635

Sleeps: 4 Bedrooms: 2 Bathrooms: 1 Pets: 1

Swiss Cottage

4 star rating

Rievaulx, near Helmsley, North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 2
  • Number of Pets: 2
  • Distance from Helmsley (miles): 2

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Price from

£585-£1629

4 star rating
Rievaulx, near Helmsley, North York Moors

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Price from

£585-£1629

Sleeps: 4 Bedrooms: 2 Bathrooms: 2 Pets: 2

Manor Farm Cottage

0 star rating

Scawton, near Helmsley, North York Moors

  • Sleeps: 3
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 3

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Price from

£325-£529

0 star rating
Scawton, near Helmsley, North York Moors

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Price from

£325-£529

Sleeps: 3 Bedrooms: 2 Bathrooms: 1 Pets: 1

Elm Tree Cottage

4 star rating

Kirkbymoorside, North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 4

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Price from

£380-£700

4 star rating
Kirkbymoorside, North York Moors

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Price from

£380-£700

Sleeps: 4 Bedrooms: 2 Bathrooms: 1 Pets: 1

Robin Lodge

3 star rating

Nawton, near Helmsley, , North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 2

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Price from

£309-£658

3 star rating
Nawton, near Helmsley, , North York Moors

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Price from

£309-£658

Sleeps: 4 Bedrooms: 2 Bathrooms: 1 Pets: 1

The Stables

5 star rating

Oswaldkirk, near Helmsley, North York Moors

  • Sleeps: 6
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 3
  • Distance from Helmsley (miles): 3

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Price from

£504-£959

5 star rating
Oswaldkirk, near Helmsley, North York Moors

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Price from

£504-£959

Sleeps: 6 Bedrooms: 2 Bathrooms: 1 Pets: 3

Highfield Barn

4 star rating

Nawton, near Helmsley, North York Moors

  • Sleeps: 2
  • Bedrooms: 1
  • Bathrooms: 1
  • Number of Pets: 0
  • Distance from Helmsley (miles): 2

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Price from

£325-£555

4 star rating
Nawton, near Helmsley, North York Moors

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Price from

£325-£555

Sleeps: 2 Bedrooms: 1 Bathrooms: 1 Pets: 0

Honeysuckle Cottage

0 star rating

Oswaldkirk, near Helmsley, North York Moors

  • Sleeps: 3
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 3

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Price from

£429-£675

0 star rating
Oswaldkirk, near Helmsley, North York Moors

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Price from

£429-£675

Sleeps: 3 Bedrooms: 2 Bathrooms: 1 Pets: 1